Substituted 2-amino-1,3,5-triazines, their preparation, and their use as herbicides and plant growth regulators

ABSTRACT

The compounds of the formula (I) and their salts  
                 
 
     where the radicals R 1  to R 4 , A 1 , A 2 , L 0 , X and n are as defined in claim 1 are suitable as herbicides and plant growth regulators and can be prepared by processes as claimed in claim 6.

[0001] The invention relates to the technical field of the cropprotection agents, such as herbicides and plant growth regulators, inparticular of the herbicides for selectively controlling harmful plantsin crops of useful plants.

[0002] It is known that 2-amino-4-(N-phenylalkylamino)-1,3,5-triazineswhich are substituted in the 6-position and which can be furthersubstituted have herbicidal and plant-growth-regulatory properties; cf.WO 97/08156 and literature cited therein, WO 99/37627 and literaturecited therein, WO 98/15537 and literature cited therein; cf. to someextent also WO 97/00254 and literature cited therein.

[0003] In some cases, the known active substances have disadvantageswhen used, be it an insufficient herbicidal action against harmfulplants, too narrow a weed plant spectrum which can be controlled with anactive substance, or too little selectivity in crops of useful plants.Other active substances cannot be prepared economically on an industrialscale, owing to precursors and reagents which are not easily available;in the case of others, the chemical stability is insufficient.

[0004] The object of the present invention is to provide alternativeactive substances of the 2-amino-1,3,5-triazine type which can beemployed as herbicides or plant-growth regulators, if appropriateadvantageously.

[0005] Subject matter of the present invention are compounds of theformula (I) and their salts

[0006] in which

[0007] R¹ is aryl, aryloxy, arylthio, arylamino,N-aryl-N-(C₁-C₄)alkylamino, (C₃-C₉)cycloalkyl, (C₃-C₉)cycloalkyloxy,(C₃-C₉)cycloalkylthio, (C₃-C₉)cycloalkylamino,N-(C₃-C₉)cycloalkyl-N-(C₁-C₄)alkylamino, di-[(C₃-C₉)cycloalkyl]amino,heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino orN-heterocyclyl-N-(C₁-C₄)alkylamino, where each of the last-mentioned 16radicals is unsubstituted or substituted, preferably unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfo, cyano,thiocyanato, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, (C₂-C₆)alkenyl,(C₂-C₆)haloalkenyl, (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₂-C₆)alkenyloxy, (C₂-C₆)haloalkenyloxy,(C₂-C₆)alkynyloxy, (C₂-C₆)haloalkynyoxy, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, mono(C₁-C₆)alkylamino, di(C₁-C₆)alkylamino,(C₃-C₉)cycloalkyl, (C₅-C₉)cycloalkenyl, [(C₁-C₅)alkyl]carbonyl,[(C₁-C₆)alkoxy]carbonyl, aminocarbonyl, mono(C₁-C₆)alkylaminocarbonyl,di(C₁-C₆)alkylaminocarbonyl, (C₁-C₆)alkylsulfonyl and(C₁-C₆)haloalkylsulfonyl, and, inclusive of substituents, preferably hasup to 30 carbon atoms, or

[0008]  is hydrogen, (C₁-C₆)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl,(C₁-C₆)alkoxy, (C₂-C₆)alkenyloxy, (C₂-C₆)alkynyloxy, (C₁-C₆)alkylthio,(C₂-C₆)alkenylthio, (C₂-C₆)alkynylthio, (C₁-C₆)alkylamino ordi-[(C₁-C₆)alkyl]amino,

[0009] where each of the last-mentioned 11 radicals can be unsubstitutedor substituted by one or more radicals selected from the groupconsisting of halogen, hydroxyl, cyano, nitro, thiocyanato,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₂-C₄)alkenyloxy,(C₂-C₄)haloalkenyloxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylthio, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)haloalkylsulfonyl, (C₃-C₉)cycloalkyl which is unsubstituted orsubstituted, phenyl which is unsubstituted or substituted, heterocyclylwhich is unsubstituted or substituted, and radicals of the formulaeR′—C(═Z′)—, R′—C(═Z′)-Z-, R′-Z-C(═Z′)—, R′R″N—C(═Z′), R′-Z-C(═Z′)—O—,R′R″N—C(═Z′)-Z-, R′-Z-C(═Z′)—NR″— and R′R″N—C(═Z′)—NR′″—,

[0010] where R′, R″ and R′″ in each case independently of one anotherare hydrogen or, preferably, (C₁-C₆)alkyl, aryl, aryl-(C₁-C₆)alkyl,(C₃-C₉)cycloalkyl or (C₃-C₉)cycloalkyl-(C₁-C₆)alkyl, where each of the 5last-mentioned radicals is unsubstituted or substituted, and where Z andZ′ independently of one another are in each case an oxygen or sulfuratom,

[0011] and, inclusive of substituents, preferably has 1 to 30 carbonatoms,

[0012] R² is (C₃-C₉)cycloalkyl which is unsubstituted or substituted,(C₄-C₉)cycloalkenyl which is unsubstituted or substituted, heterocyclylwhich is unsubstituted or substituted, or phenyl which is unsubstitutedor substituted, where R², inclusive of substituents, preferably has upto 30 carbon atoms,

[0013] R³ is a group

[0014] in which

[0015] L¹ is a direct bond, —O—, —S— or a group of the formula —NG²,preferably a direct bond,

[0016] U¹, U² independently of one another are a group of the formulaG³, OG⁴, SG⁵, NG⁸G⁷, NG⁸NG⁹G¹⁰, NG¹¹OG¹² or NG¹¹SG¹²,

[0017] U³ is a group of the formula G¹³, OG¹⁴, SG¹⁵, NG¹⁶G¹⁷,NG¹⁸NG¹⁹G²⁰, NG² OG²² or NG²³SG²⁴,

[0018] U⁴ is a group of the formula G²⁵, OG²⁶, SG²⁷ or NG²⁸G²⁹,

[0019] where the radicals G¹ to G²⁹ independently of one another arehydrogen, aryl which is unsubstituted or substituted and, inclusive ofsubstituents, preferably has 6 to 30 carbon atoms, or (C₃-C₉)cycloalkylwhich is unsubstituted or substituted and, inclusive of substituents,preferably has 3 to 30 carbon atoms, or heterocyclyl which issubstituted or unsubstituted and, inclusive of substituents, preferablyhas 2 to 30 carbon atoms, or are (C₁-C₆)alkyl, (C₂-C₆)alkenyl or(C₂-C₆)alkynyl,

[0020] where each of the last-mentioned 3 radicals is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, hydroxyl, cyano, nitro, thiocyanato, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₂-C₄)alkenyloxy, (C₂-C₄)haloalkenyloxy,(C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfinyl, (C₁-C₄)haloalkylsulfonyl, (C₃-C₉)cycloalkylwhich is unsubstituted or substituted, phenyl which is unsubstituted orsubstituted, heterocyclyl which is unsubstituted or substituted, andradicals of the formulae R′—C(═Z′)—, R′—C(═Z′)-Z-, R′-Z-C(═Z′)—,R′R″N—C(═Z′)—, R′-Z-C(═Z′)—O—, R′R″N—C(═Z′)-Z-, R′-Z-C(═Z′)—NR″— andR′R″N—C(═Z′)—NR′″—, where

[0021] R′, R″ and R′″ in each case independently of one another arehydrogen or, preferably, (C₁-C₆)alkyl, aryl, aryl-(C₁-C₆)alkyl,(C₃-C₉)cycloalkyl or (C₃-C₉)cycloalkyl-(C₁-C₆)alkyl, where each of the 5last-mentioned radicals is unsubstituted or substituted and where Z andZ′ independently of one another are in each case an oxygen or sulfuratom, and, inclusive of substituents, preferably has 1 to 30 carbonatoms,

[0022] or the radicals U¹ and U³ or U² and U⁴ or U² and G¹ or U⁴ and G¹,as a pair, together with the atoms linking them are in each case acarbocyclic or heterocyclic ring having 4 to 7 ring atoms, the ringbeing unsubstituted or substituted,

[0023] R⁴ is a radical of the formula —B¹-D¹, where B¹ and D¹ are asdefined hereinbelow, and R⁴, inclusive of substituents, preferably hasup to 20 carbon atoms,

[0024] A¹ is a direct bond or straight-chain alkylene having 1 to 5carbon atoms or straight-chain alkenylene or alkynylene having in eachcase 2 to 5 carbon atoms, where each of the three last-mentioneddiradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, nitro, cyano, thiocyanatoand radicals of the formula —B²-D², where B² and D² are as definedhereinbelow,

[0025] A² is a direct bond or straight-chain alkylene having 1 to 4carbon atoms or straight-chain alkenylene or alkynylene having in eachcase 2 to 5 carbon atoms, where each of the three last-mentioneddiradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, nitro, cyano, thiocyanatoand radicals of the formula —B³-D³, or a divalent radical of the formulaV¹, V², V³, V⁴ or V⁵,

—CR^(a)R^(b)—W*—CR^(c)R^(d)—  (V¹)

—CR^(a)R^(b)—W*—CR^(c)R^(d)—CR^(e)R^(f)—  (V²)

—CR^(a)R^(b)—CR^(c)R^(d)—W*—CR^(e)R^(f)—  (V³)

CR^(a)R^(b)—CR^(c)R^(d)W*—  (V⁴)

CR^(a)R^(b)—W*—  (V⁵),

[0026] where each of the radicals R^(a), R^(b), R^(c), R^(d), R^(e) andR^(f) in each case independently of one another is hydrogen, halogen,nitro, cyano, thiocyanato or a radical of the formula —B⁴-D⁴,

[0027] W* is in each case an oxygen atom, a sulfur atom or a group ofthe formula N(B⁵-D⁵) and

[0028] B³, B⁴, B⁵, D³, D⁴ and D⁵ are as defined hereinbelow,

[0029] B¹ and B⁵ in each case independently of one another are a directbond or a divalent group of the formulae —C(═Z*)—, —C(═Z*)-Z**-,—C(═Z*)—NH— or —C(═Z*)—NR*—, where Z*=an oxygen or sulfur atom, Z**=anoxygen or sulfur atom and R*=(C₁-C₆)alkyl, aryl, aryl-(C₁-C₆)alkyl,(C₃-C₉)cycloalkyl or (C₃-C₉)cycloalkyl-(C₁-C₆)alkyl, where each of the 5last-mentioned radicals is unsubstituted or substituted and, inclusiveof substituents, preferably has up to 20 carbon atoms,

[0030] B², B³ and B⁴ in each case independently of one another are adirect bond or a divalent group of the formulae —O—, —S(O)_(p)—,—S(O)_(p)—O—, —O—S(O)_(p)—, —CO—, —O—CO—, —CO—O—, —S—CO—, —CO—S—,—S—CS—, —CS—S—, —O—CO—O—, —NR^(O)—, —O—NR^(O)—, —NR^(O)—O—, —NR^(O)—CO—,—CO—NR^(O)—, —O—CO—NR^(O)— or —NR^(O)—CO—O—, where p is the integer 0, 1or 2 and R° is hydrogen, (C₁-C₆)alkyl, aryl, aryl-(C₁-C₆)alkyl,(C₃-C₉)cycloalkyl or (C₃-C₉)cycloalkyl-(C₁-C₆)alkyl, where each of the 5last-mentioned radicals is unsubstituted or substituted and, inclusiveof substituents, preferably has up to 20 carbon atoms,

[0031] D¹, D², D³, D⁴ and D⁵ in each case independently of one anotherare hydrogen, (C₁-C₆)alkyl, aryl, aryl-(C₁-C₆)alkyl, (C₃-C₉)cycloalkylor (C₃-C₉)cycloalkyl-(C₁-C₆)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted and, inclusive of substituents,preferably has up to 20 carbon atoms,

[0032]  or in each case two radicals D³ of two groups 3-D³ bound to onecarbon atom are linked to each other and form an alkylene group having 2to 4 carbon atoms which is unsubstituted or substituted by one or moreradicals selected from the group consisting of (C₁-C₄)alkyl and(C₁-C₄)alkoxy,

[0033] L^(o) is a direct bond, oxygen, sulfur or a group NG³⁰ in whichthe radical G³⁰ is hydrogen, aryl which is unsubstituted or substitutedand, inclusive of substituents, preferably has 6 to 30 carbon atoms, or(C₃-C₉)cycloalkyl which is unsubstituted or substituted and, inclusiveof substituents, preferably has 3 to 30 carbon atoms, or heterocyclylwhich is substituted or unsubstituted and, inclusive of substituents,preferably has 2 to 30 carbon atoms, or is (C₁-C₆)alkyl, (C₂-C₆)alkenylor (C₂-C₆)alkynyl,

[0034] where each of the last-mentioned 3 radicals is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, hydroxyl, cyano, nitro, thiocyanato, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₂-C₄)alkenyloxy, (C₂-C₄)haloalkenyloxy,(C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfinyl, (C₁-C₄)haloalkylsulfonyl, (C₃-C₉)cycloalkylwhich is unsubstituted or substituted, phenyl which is unsubstituted orsubstituted, heterocyclyl which is unsubstituted or substituted, andradicals of the formulae R′—C(═Z′)—, R′—C(═Z′)-Z-, R′-Z-C(═Z′)—,R′R″N—C(═Z′)—, R′-Z-C(═Z′)—O—, R′R″N—C(═Z′)-Z-, R′-Z-C(═Z′)—NR″— andR′R″N—C(═Z′)—NR′″—, where

[0035] R′, R″ and R′″ in each case independently of one another arehydrogen or, preferably, (C₁-C₆)alkyl, aryl, aryl-(C₁-C₆)alkyl,(C₃-C₉)cycloalkyl or (C₃-C₉)cycloalkyl-(C₁-C₆)alkyl, where each of the 5last-mentioned radicals is unsubstituted or substituted and where Z andZ′ independently of one another are in each case an oxygen or sulfuratom,

[0036] and, inclusive of substituents, preferably has 1 to 30 carbonatoms,

[0037] (X)_(n) is n substituents X, where the X in each caseindependently of one another are halogen, hydroxyl, amino, nitro,formyl, carboxyl, cyano, thiocyanato, aminocarbonyl or (C₁-C₆)alkyl,(C₁-C₆)alkoxy, (C₁-C₆)alkylthio, mono(C₁-C₆)alkylamino,di(C₁-C₄)alkylamino, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl,[(C₁-C₆)alkyl]carbonyl, [(C₁-C₆)alkoxy]carbonyl,mono(C₁-C₆)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,N-(C₁-C₆)alkanoylamino or N-(C₁-C₄)alkanoyl-N-(C₁-C₄)alkylamino,

[0038] where each of the last-mentioned 13 radicals is unsubstituted orsubstituted, preferably unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, hydroxyl, amino,nitro, formyl, carboxyl, cyano, thiocyanato, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₃-C₉)cycloalkyl,(C₃-C₉)cycloalkylamino, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, phenyl, phenoxy, phenylthio,phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio andheterocyclylamino,

[0039] where each of the last-mentioned 8 radicals is unsubstituted orhas one or more substituents selected from the group consisting ofhalogen, nitro, cyano, (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, formyl, (C₁-C₄)alkylcarbonyl and(C₁-C₄)alkoxycarbonyl,

[0040]  or is (C₃-C₉)cycloalkyl, (C₃-C₉)cycloalkoxy,(C₃-C₉)cycloalkylamino, phenyl, phenoxy, phenylthio, phenylcarbonyl,heterocyclyl, heterocyclyloxy, heterocyclylthio or heterocyclylamino,

[0041] where each of the last-mentioned 11 radicals is unsubstituted orsubstituted, preferably unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, hydroxyl, amino,nitro, formyl, carboxyl, cyano, thiocyanato, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₉)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl andDi(C₁-C₄)alkylaminocarbonyl,

[0042]  or two adjacent radicals X together are a fused cycle having 4to 6 ring atoms which is carbocyclic or contains hetero ring atomsselected from the group consisting of O, S and N and which isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)alkyl and oxo,

[0043] n is 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2, 3 or 4, inparticular 0, 1 or 2, and heterocyclyl in the abovementioned radicalsindependently of one another in each case is a heterocyclic radicalhaving 3 to 7 ring atoms and 1 to 3 hetero atoms selected from the groupconsisting of N, O and S. Unless specified in greater detail, divalentradicals, for example B¹=—C(═Z*)-Z**-, are defined such that, in thecomposite groups, for example —B¹-D¹, it is the bond of the divalentradical that is written on the right in the formula for the divalentradical which is linked to the group D¹, i.e. —B¹-D¹ is a group of theformula —C(═Z*)-Z**-D¹; this applies similarly to analogous divalentradicals.

[0044] The compounds of the formula (I) can form salts by addition of asuitable inorganic or organic acid such as, for example, HCl, HBr, H₂SO₄or HNO₃, but also oxalic acid or sulfonic acids, to a basic group suchas, for example, amino or alkylamino. Suitable substituents which arepresent in deprotonated form such as, for example, sulfonic acids orcarboxylic acids, can form internal salts with groups which areprotonable themselves, such as amino groups. Likewise, salts can beformed by replacing the hydrogen in suitable substituents such as, forexample, sulfonic acids or carboxylic acids, by an agriculturallysuitable cation. These salts are, for example, metal salts, inparticular alkali metal salts or alkaline earth metal salts, inparticular sodium salts and potassium salts, or else ammonium salts,salts with organic amines, or quaternary ammonium salts.

[0045] In formula (I) and all subsequent formulae, the radicals alkyl,alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and thecorresponding unsaturated and/or substituted radicals can be in eachcase straight-chain or branched in the carbon skeleton. Unlessspecifically indicated, the lower carbon skeletons, for example thosehaving 1 to 6 carbon atoms or, in the case of unsaturated groups, 2 to 6carbon atoms, are preferred for these radicals. Alkyl radicals, also inthe composite meanings such as alkoxy, haloalkyl and the like, are, forexample, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls,hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls, such asn-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynylradicals have the meanings of the possible unsaturated radicals whichcorrespond to the alkyl radicals; alkenyl is, for example, allyl,1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl,but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl; alkynylis, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl,1-methylbut-3-yn-1-yl.

[0046] Cycloalkyl is a carbocyclic, saturated ring system havingpreferably 3-8 carbon atoms, for example cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl. In the case of substituted cycloalkyl, thisencompasses cyclic systems with substituents, where the substituents arebonded to the cycloalkyl radical by a double bond, for example, analkylidene group such as methylidene. In the case of substitutedcycloalkyl, this also encompasses polycyclic aliphatic systems such as,for example, bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl,bicyclo[2.1.0]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl,bicyclo[2.1.0]pentan-5-yl, adamantan-1-yl and adamantan-2-yl.

[0047] Cycloalkenyl is a carbocyclic, nonaromatic, partially unsaturatedring system having preferably 4-8 carbon atoms, for example1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl,3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl,1,3-cyclohexadienyl or 1,4-cyclohexadienyl. In the case of substitutedcycloalkenyl, what has been said for substituted cycloalkyl appliesanalogously.

[0048] Halogen is, for example, fluorine, chlorine, bromine or iodine.Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl or alkynyl,respectively, each of which is partially or fully substituted by,preferably, fluorine, chlorine and/or bromine, in particular by fluorineor chlorine, for example monohaloalkyl, perhaloalkyl, CF₃, CHF₂, CH₂F,CF₃CF₂, CH₂FCHCl, CCl₃, CHCl₂, CH₂CH₂Cl; haloalkoxy is, for example,OCF₃, OCHF₂, OCH₂F, CF₃CF₂O, OCH₂CF₃ and OCH₂CH₂Cl; this also appliesanalogously to haloalkenyl and other halogen-substituted radicals.

[0049] Aryl is a mono-, bi- or polycyclic aromatic system, for examplephenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl,fluorenyl and the like, preferably phenyl.

[0050] A heterocyclic radical or ring (heterocyclyl) can be saturated,unsaturated or heteroaromatic; it preferably contains one or more, inparticular 1, 2 or 3, hetero atoms in the heterocyclic ring, preferablyselected from the group consisting of N, O and S; it is preferably analiphatic heterocyclyl radical having 3 to 7 ring atoms or aheteroaromatic radical having 5 or 6 ring atoms. The heterocyclicradical can be, for example, a heteroaromatic radical or ring(heteroaryl) such as, for example, a mono-, bi- or polycyclic aromaticsystem in which at least 1 ring contains one or more hetero atoms, forexample pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl,thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, furyl, pyrrolyl,pyrazolyl, imidazolyl and triazolyl, or it is a partially or fullyhydrogenated radical such as oxiranyl, oxetanyl, oxolanyl(=tetrahydrofuryl), oxanyl, pyrrolidyl, piperidyl, piperazinyl,dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl andmorpholinyl. Suitable substituents for a substituted heterocyclicradical are the substituents stated further below, and additionally alsooxo. The oxo group can also be present at those hetero ring atoms wherevarious oxidation numbers are possible, for example in the case of N andS.

[0051] Substituted radicals such as a substituted alkyl, alkenyl,alkynyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radical are,for example, a substituted radical which is derived from theunsubstituted skeleton, the substituents being, for example, one ormore, preferably 1, 2 or 3, radicals selected from the group consistingof halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro,carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl,carbamoyl, mono- and dialkylaminocarbonyl, substituted amino such asacylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl,alkylsulfonyl, haloalkylsulfonyl and, in the case of cyclic radicals,also alkyl and haloalkyl.

[0052] In this context, “one or more radicals selected from the groupconsisting of” in the definition are to be understood as meaning in eachcase one or more identical or different radicals selected from thestated group of radicals, unless specific limitations are definedexpressly.

[0053] The term “substituted radicals' such as substituted alkyl and thelike includes, in addition to the saturated hydrocarbon-containingradicals stated, corresponding unsaturated aliphatic and aromaticradicals such as unsubstituted or substituted alkenyl, alkynyl,alkenyloxy, alkynyloxy, phenyl, phenoxy and the like, as substituents.In the case of substituted cyclic radicals with aliphatic moieties inthe ring, this also encompasses cyclic systems with those substituentswhich are bonded to the ring by a double bond, for example which aresubstituted by an alkylidene group such as methylidene or ethylidene.

[0054] In the case of radicals with carbon atoms, those having 1 to 4carbon atoms, in particular 1 or 2 carbon atoms, are preferred.Substituents which are preferred are, as a rule, those selected from thegroup consisting of halogen, e.g. fluorine and chlorine, (C₁-C₄)alkyl,preferably methyl or ethyl, (C₁-C₄)haloalkyl, preferablytrifluoromethyl, (C₁-C₄)alkoxy, preferably methoxy or ethoxy,(C₁-C₄)haloalkoxy, nitro and cyano. Especially preferred in this contextare the substituents methyl, methoxy and chlorine.

[0055] Mono- or disubstituted amino is a chemically stable radicalselected from the group consisting of substituted amino radicals whichare N-substituted by, for example, one or two identical or differentradicals selected from the group consisting of alkyl, alkoxy, acyl andaryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino,N-alkyl-N-arylamino and N-heterocycles; preferred in this context arealkyl radicals having 1 to 4 carbon atoms; aryl is preferably phenyl orsubstituted phenyl in this context; acyl is as defined further below,preferably (C₁-C₄)alkanoyl. This also applies analogously to substitutedhydroxylamino or hydrazino.

[0056] Unsubstituted or substituted phenyl is preferably phenyl which isunsubstituted or mono- or polysubstituted, preferably up totrisubstituted, by identical or different radicals selected from thegroup consisting of halogen, (C₁-C₄)alkyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy and nitro, for example o-, m- andp-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and4-trifluoro- and -trichlorophenyl, 2,4-, 3,5-, 2,5- and2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.

[0057] An acyl radical is, in a broad sense, the radical of an organicacid which is formed formally by removing an OH group, for example theradical of a carboxylic acid and radicals of acids derived therefrom,such as thiocarboxylic acid, unsubstituted or N-substitutediminocarboxylic acids or the radical of carbonic monoesters,unsubstituted or N-substituted carbamic acid, sulfonic acids, sulfinicacids, phosphonic acids, and phosphinic acids. Acyl is, for example,formyl, alkylcarbonyl such as [(C₁-C₄)alkyl]carbonyl, phenylcarbonyl,alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl,alkylsulfinyl, N-alkyl-1-iminoalkyl and other radicals of organic acids.In this context, the radicals can be even further substituted in each ofthe alkyl or phenyl moieties, for example in the alkyl moiety by one ormore radicals selected from the group consisting of halogen, alkoxy,phenyl and phenoxy; examples of substituents in the phenyl moiety arethe substituents which have already been mentioned further above ingeneral for substituted phenyl. Acyl in the narrower sense is, forexample, the radical of an alkanoic acid, alkenoic acid, alkynoic acid,arylcarboxylic acid (for example benzoyl), alkoxycarbonyl,alkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, alkylsulfonylor alkysulfinyl; in an even narrower sense, acyl is a radical of analkanoic acid, for example a (C₁-C₂₄)alkanoic acid, preferably(C₁-C₁₈)alkanoic acid, in particular (C₁-C₁₂)alkanoic acid, veryespecially (C₁-C₆)alkanoic acid such as formyl, acetyl or propionyl.

[0058] By combination of variables the generic formulae may formallydefine instable functional groups, e.g. the carbamyl radical or thehydroxy carbonyloxy radical, which are instable in neutral or acidicaqueous medium and which thus are not preferred or are used by way oftheir stable salts or degradation products only, respectively.

[0059] Subject matter of the invention are all stereoisomers which areencompassed by formula (I), and their mixtures. Such compounds of theformula (I) contain one or more asymmetric carbon atoms or else doublebonds which are not stated specifically in the formula (I). The possiblestereoisomers which are defined by their specific spatial form, such asenantiomers, diastereomers, Z- and E-isomers, are all encompassed byformula (I) and can be obtained by customary methods from mixtures ofthe stereoisomers, or else be prepared by stereoselective reactions incombination with the use of stereochemically pure starting materials.

[0060] Compounds of the stated formula (I) according to the invention ortheir salts in which individual radicals have one of the preferredmeanings which have already been stated or are stated hereinbelow, or inparticular those in which one or more of the preferred meanings whichhave already been stated or which are stated hereinbelow are combined,are of particular interest, mainly because of the more potent herbicidalaction, better selectivity and/or greater ease of preparation.

[0061] R¹ is preferably phenyl, phenoxy, phenylthio, phenylamino,N-phenyl-N-(C₁-C₄)alkylamino, where each of the last-mentioned 5radicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, hydroxyl, amino, nitro,formyl, carboxyl, sulfo, cyano, thiocyanato, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₉)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonyl and(C₁-C₄)haloalkylsulfonyl and, inclusive of substituents, has 6 to 30carbon atoms, preferably 6 to 20 carbon atoms, in particular 6 to 15carbon atoms. In this context, R¹ is, in particular, phenyl which isunsubstituted or substituted.

[0062] R¹ is preferably also (C₃-C₉)cycloalkyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, hydroxyl, amino, cyano, thiocyanato, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino and di(C₁-C₄)alkylamino and,inclusive of substituents, has 3 to 30 carbon atoms, preferably 3 to 20carbon atoms, in particular 3 to 15 carbon atoms. In this context, R¹is, in particular, (C₃-C₆)cycloalkyl which is unsubstituted orsubstituted.

[0063] R¹ is preferably also heterocyclyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfonyl, cyano,thiocyanato, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₃-C₉)cycloalkyl,[(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl, aminocarbonyl,mono(C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulfonyl and (C₁-C₄)haloalkylsulfonyl and, inclusive ofsubstituents, has 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms,in particular 2 to 15 carbon atoms.

[0064] In this context, and also in other radicals, heterocyclyl is asdefined further above in general terms or by preference.

[0065] In particular, heterocyclyl preferably is, in this context, aheterocyclic radical having 3 to 7, in particular 3 to 6, ring atoms andone hetero atom selected from the group consisting of N, O and S, forexample pyridyl, thienyl, furyl, pyrrolyl, oxiranyl, oxetanyl, oxolanyl(=tetrahydrofuryl), oxanyl, pyrrolidyl, piperidyl, or is a heterocyclicradical having two or three hetero atoms selected from the groupconsisting of pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl,thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl,piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl,isoxazolidinyl, morpholinyl.

[0066] R¹ is preferably also hydrogen or, in particular, (C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₁-C₆)alkoxy or (C₁-C₆)alkylthio,

[0067] where each of the last-mentioned 5 radicals is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, hydroxyl, cyano, nitro, thiocyanato, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₂-C₄)alkenyloxy, (C₂-C₄)haloalkenyloxy,(C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfinyl, (C₁-C₄)haloalkylsulfonyl and

[0068] (C₃-C₆)cycloalkyl, which is unsubstituted or substituted by oneor more radicals selected from the group consisting of halogen,hydroxyl, amino, cyano, thiocyanato, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino and di(C₁-C₄)alkylamino, andphenyl and heterocyclyl, where each of the two last-mentioned radicalsis unsubstituted or substituted by one or more radicals selected fromthe group consisting of halogen, hydroxyl, amino, nitro, formyl,carboxyl, sulfonyl, cyano, thiocyanato, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₉)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonyl and(C₁-C₄)haloalkylsulfonyl, and radicals of the formulae R′—C(═Z′)—,R′—C(═Z′)-Z-, R′-Z-C(═Z′)—, R′R″N—C(═Z′)—, R′-Z-C(═Z′)—O—,R′R″N—C(═Z′)-Z-, R′-Z-C(═Z′)—NR″— and R′R″N—C(═Z′)—NR′″—, where R′, R″and R′″ in each case independently of one another are hydrogen or, inparticular, (C₁-C₄)alkyl, phenyl, phenyl(C₁-C₄)alkyl, (C₃-C₆)cycloalkylor (C₃-C₆)cycloalkyl-(C₁-C₄)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, hydroxyl, amino, nitro,formyl, cyano, thiocyanato, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₂-C₄)alkenyl,(C₂-C₄)alkynyl, (C₃-C₆)cycloalkyl and, in the case of cyclic radicals,also (C₁-C₄)alkyl and (C₁-C₄)haloalkyl, and where Z and Z′ independentlyof one another are in each case an oxygen or sulfur atom, and, inclusiveof substituents, preferably has 1 to 20 carbon atoms, in particular 1 to15 carbon atoms,

[0069] R¹ is furthermore preferably

[0070] (C₁-C₄)alkyl which is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, (C₁-C₄)alkoxy,(C₁-C₄)alkylthio, (C₁-C₄)alkylsulfonyl and (C₃-C₉)cycloalkyl which isunsubstituted or substituted, and

[0071] phenyl which is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, (C₁-C₄)alkyl and(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,amino, mono- and di[(C₁-C₄)alkyl]amino, (C₁-C₄)alkanoylamino,benzoylamino, nitro, cyano, [(C₁-C₄)alkyl]carbonyl, formyl, carbamoyl,mono- and di-[(C₁-C₄)alkyl]aminocarbonyl and (C₁-C₄)alkylsulfonyl, and

[0072] heterocyclyl having 3 to 6 ring atoms and 1 to 3 hetero ringatoms selected from the group consisting of N, O and S, where the ringis unsubstituted or substituted by one or more radicals selected fromthe group consisting of halogen, (C₁-C₄)alkyl and oxo, or

[0073] phenyl which is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, hydroxyl, amino,nitro, formyl, carboxyl, sulfonyl, cyano, thiocyanato, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₉)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonyl and(C₁-C₄)haloalkylsulfonyl and, inclusive of substituents, has 2 to 30carbon atoms, preferably 2 to 20 carbon atoms, in particular 2 to 15carbon atoms.

[0074] R¹ is furthermore preferably (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,benzyl or [(C₃-C₆)cycloalkyl]-(C₁-C₂)alkyl, in particular (C₁-C₄)alkyl,(C₁-C₄)haloalkyl or [(C₃-C₆)cycloalkyl]methyl, very especially —CH₃,—CH₂F, —CHF₂, —CF₃, —CH₂Cl, —CHCl₂, —CCl₃, —CH₂Br, —CHBr₂, —CH₂CH₃,—CH₂CH₂F, —CF₂CHF₂, —CH₂CH₂Cl, —CHFCH₃, —CHFCH₂CH₃, —CH₂CH₂Br,—CH(CH₃)₂, —CF(CH₃)₂, —C(CH₃)₂Cl, —CH₂CH₂CH₂F, —CH₂CH₂CH₂Cl orcyclopropylmethyl or 1-fluorocycloprop-1-yl.

[0075] Other preferred compounds (I) according to the invention arethose in which

[0076] R¹ is aryl which is unsubstituted or substituted and, inclusiveof substituents, preferably has 6 to 30 carbon atoms, or(C₃-C₉)cycloalkyl which is unsubstituted or substituted and, inclusiveof substituents, preferably has 3 to 30 carbon atoms, or heterocyclylwhich is unsubstituted or substituted and, inclusive of substituents,preferably has 2 to 30 carbon atoms, or is (C₁-C₆)alkyl, (C₂-C₆)alkenylor (C₂-C₆)alkynyl,

[0077] where each of the last-mentioned 3 radicals is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, hydroxyl, cyano, nitro, thiocyanato, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₂-C₄)alkenyloxy, (C₂-C₄)haloalkenyloxy,(C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfinyl, (C₁-C₄)haloalkylsulfonyl, (C₃-C₉)cycloalkylwhich is unsubstituted or substituted, phenyl which is unsubstituted orsubstituted, heterocyclyl which is unsubstituted or substituted, andradicals of the formulae R′—C(═Z′)—, R′—C(═Z′)-Z-, R′-Z-C(═Z′)—,R′R″N—C(═Z′)—, R′-Z-C(═Z′)—O—, R′R″N—C(═Z′)-Z-, R′-Z-C(═Z′)—NR″— andR′R″N—C(═Z′)—NR′″—, where R′, R″ and R′″ in each case independently ofone another are (C₁-C₆)alkyl, aryl, aryl-(C₁-C₆)alkyl, (C₃-C₉)cycloalkylor (C₃-C₉)cycloalkyl-(C₁-C₆)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted and where Z and Z′independently of one another are in each case an oxygen or sulfur atom,and, inclusive of substituents, preferably has 1 to 30 carbon atoms,

[0078] R¹ is preferably also phenyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfo, cyano,thiocyanato, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₃-C₉)cycloalkyl,[(C₁-C₄)alkyl]carbonyl, [(C(—C₄)alkoxy]carbonyl, aminocarbonyl,mono(C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulfonyl and (C₁-C₄)haloalkylsulfonyl and, inclusive ofsubstituents, has 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms,in particular 6 to 15 carbon atoms.

[0079] Independently of the radicals R¹, R³, R⁴, L^(o), A¹, A² and(X)_(n) and preferably in combination with preferred meanings of one ormore of these radicals, the following meanings of R² are of particularinterest.

[0080] R² is preferably (C₃-C₉)cycloalkyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof the radicals A), B), C) and D), where

[0081] group A) consists of the radicals halogen, hydroxyl, amino,nitro, formyl, carboxyl, aminocarbonyl, sulfo, cyano, thiocyanato andoxo,

[0082] group B) consists of the radicals (C₁-C₆)alkyl, (C₁-C₆)alkoxy,(C₁-C₆)alkylthio, mono(C₁-C₆)alkylamino, di(C₁-C₄)alkylamino,(C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₉)cycloalkyl, (C₄-C₉)cycloalkenyl,(C₁-C₆)alkylidene, (C₄-C₉)cycloalkylidene, radicals of the formulaeR′—C(═Z′)—, R′—C(═Z′)-Z-, R′-Z-C(═Z′)—, R′R″N—C(═Z′)—, R′-Z-C(═Z′)—O—,R′R″N—C(═Z′)-Z-, R′-Z-C(═Z′)—NR″— and R′R″N—C(═Z′)—NR′″—, where R′, R″and R′″ in each case independently of one another are hydrogen or, inparticular, (C₁-C₆)alkyl, phenyl, phenyl-(C₁-C₆)alkyl, (C₃-C₉)cycloalkylor (C₃-C₉)cycloalkyl-(C₁-C₆)alkyl and where Z and Z′ independently ofone another are in each case an oxygen or sulfur atom,

[0083] group C) consists of radicals as defined for group B), but whereeach radical is substituted by one or more radicals selected from thegroup consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl,sulfo, cyano, thiocyanato, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino,di(C₁-C₄)alkylamino, (C₃-C₉)cycloalkyl, (C₄-C₉)cycloalkylene(C₄-C₉)cycloalkylidene, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, phenyl, phenoxy, phenylthio,phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio andheterocyclylamino,

[0084] where each of the last-mentioned 21 radicals is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, nitro, cyano, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkoxy, formyl, (C₁-C₄)alkylcarbonyl and(C₁-C₄)alkoxycarbonyl and, in the case of cyclic radicals, also(C₁-C₄)alkyl, (C₁-C₄)haloalkyl and (C₁-C₆)alkylidene,

[0085]  and, in the case of cyclic radicals, also (C₁-C₆)alkyl,(C₁-C₆)haloalkyl and (C₁-C₆)alkylidene, and

[0086] group D) consists of divalent or trivalent aliphatic bridgeshaving 1 to 6, preferably 1 to 4, carbon atoms which, in the case ofdivalent bridges, connect two and, in the case of trivalent bridges,three carbon atoms of the cyclic skeleton and the radical R² thusconstitutes the radical of a bicyclic or tricyclic system, where each ofthe bridges is unsubstituted or substituted by one or more substituentsselected from the group consisting of halogen, nitro, cyano,(C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkyl,(C₁-C₄)haloalkoxy, formyl, (C₁-C₄)alkylcarbonyl, (C₁-C₄)alkoxycarbonyland oxo,

[0087]  and where R², inclusive of substituents, preferably has 3 to 20carbon atoms, in particular 3 to 15 carbon atoms. Preferred(C₃-C₉)cycloalkyl radicals are, in this context, cyclopropyl,cyclobutyl, cyclopentyl or cyclohexyl, in particular cyclopropyl,cyclobutyl or cyclopentyl.

[0088] R² is preferably also (C₄-C₉)cycloalkenyl which is unsubstitutedor substituted by one or more radicals selected from the groupconsisting of the radicals A), B), C) and D), as are defined as radicalsfor the case R²=(C₃-C₉)cycloalkyl, and, inclusive of substituents,preferably has 4 to 20 carbon atoms, in particular 4 to 15 carbon atoms.

[0089] Preferred (C₄-C₉)cycloalkenyl radicals are 1-cyclobutenyl,2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl and 3-cyclopentenyl.

[0090] R² is preferably also heterocyclyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof the radicals A), B), C) and D), as are defined as radicals for thecase R²=(C₃-C₉)cycloalkyl.

[0091] In this context, heterocyclyl is preferably a heterocyclicradical having 3 to 6 ring atoms and one heteroring atom, in particular,a radical selected from the group consisting of pyridyl, thienyl, furyl,pyrrolyl, oxiranyl, 2-oxetanyl, 3-oxetanyl, oxolanyl (=tetrahydrofuryl),pyrrolidyl, piperidyl, in particular oxiranyl, 2-oxetanyl, 3-oxetanyl oroxolanyl, or is a heterocyclic radical having two or three hetero atoms,for example pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl,thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl,piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl,isoxazolidinyl or morpholinyl.

[0092] R² is preferably also phenyl which is unsubstituted orsubstituted by one or more radicals selected from the group of theradicals A), B) and C) as are defined as radicals forR²=(C₃-C₉)cycloalkyl.

[0093] Inclusive of substituents, R² preferably has up to 20 carbonatoms, in particular up to 15 carbon atoms, very especially up to 10carbon atoms.

[0094] R² is preferably (C₃-C₉)cycloalkyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof the radicals A), B), C) and D),

[0095] where

[0096] group A) consists of the radicals halogen, hydroxyl, nitro,formyl, aminocarbonyl, cyano and thiocyanato,

[0097] group B) consists of the radicals (C₁-C₄)alkyl, (C₁-C₄)alkoxy,(C₁-C₄)alkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₃-C₆)cycloalkyl, (C₄-C₆)cycloalkenyl,(C₁-C₄)alkylidene, (C₄-C₆)cycloalkylidene, radicals of the formulaeR′—C(═Z′)—, R′—C(═Z′)-Z-, R′-Z-C(═Z′)—, R′R″N—C(═Z′), R′-Z-C(═Z′)—O—,R′R″N—C(═Z′)-Z-, R′-Z-C(═Z′)—NR″— and R′R″N—C(═Z′)—NR′″—, where R′, R″and R′″ in each case independently of one another are hydrogen or, inparticular, (C₁-C₄)alkyl, phenyl, phenyl-(C₁-C₄)alkyl, (C₃-C₆)cycloalkylor (C₃-C₆)cycloalkyl-(C₁-C₆)alkyl and where Z and Z′ independently arein each case one oxygen or sulfur atom,

[0098] group C) consists of radicals as shown for group B), but whereeach radical is substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino,di(C₁-C₄)alkylamino, (C₃-C₆)cycloalkyl, [(C₁-C₄)alkyl]carbonyl,[(C₁-C₄)alkoxy]carbonyl, aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, phenyl, phenoxy, phenylthio,phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio andheterocyclylamino,

[0099] where each of the last-mentioned 8 radicals is unsubstituted orhas one or more substituents selected from the group consisting ofhalogen, nitro, cyano, (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylcarbonyl and(C₁-C₄)alkoxycarbonyl, and

[0100] group D) consists of divalent aliphatic bridges which connect twocarbon atoms of the cyclic skeleton and the radical R² thus representsthe radical of a bicyclic system, for example bicyclo[1.1.0]butan-1-yl,bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl,bicyclo[2.1.0]pentan-2-yl or bicyclo[2.1.0]pentan-5-yl, where each ofthe bridges is unsubstituted or substituted by one or more substituentsselected from the group consisting of halogen, (C₁-C₄)alkyl,(C₁-C₄)alkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy,(C₁-C₄)alkylcarbonyl, (C₁-C₄)alkoxycarbonyl and oxo.

[0101] R² is especially preferably (C₃-C₉)cycloalkyl which isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, hydroxyl, cyano, thiocyanato, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, (C₁-C₄)alkylidene, mono(C₁-C₄)alkylamino anddi(C₁-C₄)alkylamino,

[0102] or is heterocyclyl or phenyl, where each of the last-mentionedtwo radicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, hydroxyl, amino, nitro,formyl, carboxyl, sulfonyl, cyano, thiocyanato, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₆)cycloalkyl, heterocyclyl having 3 to 6 ring atoms,[(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl, aminocarbonyl,mono(C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulfonyl and (C₁-C₄)haloalkylsulfonyl.

[0103] Independently of the radicals R¹, R², R⁴, A¹, A², L^(o) and(X)_(n), and preferably in combination with preferred meanings of one ormore of these radicals, the following meanings of R³ are of particularinterest:

[0104] where the radicals R⁵ to R¹⁷ are defined further below.

[0105] Also of particular interest are compounds

[0106] in which

[0107] R⁶ and R⁷ together with the nitrogen atom of the group NR⁶R⁷,

[0108] R⁷ and OR⁸ together with the nitrogen atom of the group NOR⁸R¹,

[0109] R⁷ and SR⁸ together with the nitrogen atom of the group NSR⁸R⁷,

[0110] R¹⁰ and R¹¹ together with the nitrogen atom of the group NR¹⁰R¹¹,

[0111] OR¹² and OR¹³ or SR¹² and SR¹³ together with the carbon atom ofthe groups of the formulae

[0112] respectively,

[0113] OR⁹ and R¹⁴ or SR⁹ and R¹⁴ together with the carbon atom of thegroups

[0114] respectively,

[0115] R¹⁴ and R¹⁵ together with the carbon atom of the group

[0116] R⁵ and R⁷ together with the atom group

[0117] R⁵ and R¹⁷ together with the carbon atom of the group

[0118] R⁵ and R¹⁶ together with the atom group

[0119] R⁷ and R¹⁰ together with the atom group

[0120] in each case independently of one another form a carbocyclic orheterocyclic ring having 3 to 7 ring atoms and 1 to 6 hetero atoms,where the optional further hetero ring atoms are selected from the groupconsisting of N, O and S and the carbocyclic or heterocyclic ring is ineach case unsubstituted or substituted,

[0121] the radicals R⁵ to R¹⁷ being defined hereinbelow.

[0122] In the above formulae for atom groups, the symbol for a doublebond “═” which has substituents on one side only (unilateral doublebond) denotes the bonding site of a double bond (═a free double bond,synonymous with the binding sites of an ylidene radical) and not theabbreviated form of vinyl.

[0123] R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹⁴, R¹⁵, R¹⁶, R¹⁷ in the aboveformulae independently of one another are

[0124] hydrogen, aryl which is unsubstituted or substituted and,inclusive of substituents, preferably has 6 to 30 carbon atoms, or(C₃-C₉)cycloalkyl which is unsubstituted or substituted and, inclusiveof substituents, preferably has 3 to 30 carbon atoms, or heterocyclylwhich is unsubstituted or substituted and, inclusive of substituents,preferably has 2 to 30 carbon atoms, or (C₁-C₆)alkyl, (C₂-C₆)alkenyl or(C₂-C₆)alkynyl,

[0125] where each of the last-mentioned 3 radicals is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, hydroxyl, cyano, nitro, thiocyanato, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₂-C₄)alkenyloxy, (C₂-C₄)haloalkenyloxy,(C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfinyl, (C₁-C₄)haloalkylsulfonyl, (C₃-C₉)cycloalkylwhich is unsubstituted or substituted, phenyl which is unsubstituted orsubstituted, heterocyclyl which is unsubstituted or substituted, andradicals of the formulae R′—C(═Z′)—, R′—C(═Z′)-Z-, R′-Z-C(═Z′)—,R′R″N—C(═Z′)—, R′-Z-C(═Z′)—O—, R′R″N—C(═Z′)-Z-, R′-Z-C(═Z′)—NR″— andR′R″N—C(═Z′)—NR′″—,

[0126] where R′, R″ and R′″ in each case independently of one anotherare hydrogen or, in particular, (C₁-C₆)alkyl, aryl, aryl-(C₁-C₆)alkyl,(C₃-C₉)cycloalkyl or (C₃-C₉)cycloalkyl-(C₁-C₆)alkyl, where each of the 5last-mentioned radicals is unsubstituted or substituted and where Z andZ′ independently of one another are in each case an oxygen or sulfuratom,

[0127] and, inclusive of substituents, preferably has 1 to 30 carbonatoms.

[0128] R¹², R¹³ in each case independently of one another are

[0129] aryl which is unsubstituted or substituted and, inclusive ofsubstituents, preferably has 6 to 30 carbon atoms, or (C₃-C₉)cycloalkylwhich is unsubstituted or substituted and, inclusive of substituents,preferably has 3 to, 30 carbon atoms, or heterocyclyl which isunsubstituted or substituted and, inclusive of substituents, preferablyhas 2 to 30 carbon atoms, or are (C₁-C₆)alkyl, (C₂-C₆)alkenyl or(C₂-C₆)alkynyl,

[0130] where each of the last-mentioned 3 radicals is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, hydroxyl, cyano, nitro, thiocyanato, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₂-C₄)alkenyloxy, (C₂-C₄)haloalkenyloxy,(C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfinyl, (C₁-C₄)haloalkylsulfonyl, (C₃-C₉)cycloalkylwhich is unsubstituted or substituted, phenyl which is unsubstituted orsubstituted, heterocyclyl which is unsubstituted or substituted, andradicals of the formulae R′—C(═Z′)—, R′—C(═Z′)-Z-, R′-Z-C(═Z′)—,R′R″N—C(═Z′)—, R′-Z-C(═Z′)—O—, R′R″N—C(═Z′)-Z-, R′-Z-C(═Z′)—NR″— andR′R″N—C(═Z′)—NR′″—,

[0131] where R′, R″ and R′″ in each case independently of one anotherare hydrogen or, in particular, (C₁-C₆)alkyl, aryl, aryl-(C₁-C₆)alkyl,(C₃-C₉)cycloalkyl or (C₃-C₉)cycloalkyl-(C₁-C₆)alkyl, where each of the 5last-mentioned radicals is unsubstituted or substituted and where Z andZ′ independently of one another are in each case one oxygen or sulfuratom,

[0132] and, inclusive of substituents, preferably has 1 to 30 carbonatoms.

[0133] Preferably, the radicals R⁵, R⁶, R⁷, R⁸, R⁹, R₁₀, R¹¹, R¹⁴ R¹⁵,R¹⁶, R¹⁷ independently of one another are hydrogen.

[0134] Preferably, the radicals R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹⁴ R¹⁵,R¹⁶, R¹⁷ in each case independently of one another are also

[0135] phenyl which is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, hydroxyl, amino,nitro, formyl, carboxyl, sulfo, cyano, thiocyanato, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₉)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonyl and(C₁-C₄)haloalkylsulfonyl and, inclusive of substituents, has 6 to 30carbon atoms, preferably 6 to 20 carbon atoms, in particular 6 to 15carbon atoms.

[0136] Preferably, the radicals R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹⁴, R¹⁵,R¹⁶, R¹⁷ in each case independently of one another are also

[0137] (C₃-C₉)cycloalkyl which is unsubstituted or substituted by one orradicals selected from the group consisting of halogen, hydroxyl, amino,cyano, thiocyanato, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,mono(C₁-C₄)alkylamino and di(C₁-C₄)alkylamino and, inclusive ofsubstituents, has 3 to 30 carbon atoms, preferably 3 to 20 carbon atoms,in particular 3 to 15 carbon atoms.

[0138] Preferably, the radicals R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹⁴, R¹⁵,R¹⁶, R¹⁷ in each case independently of one another are also

[0139] heterocyclyl which is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, hydroxyl, amino,nitro, formyl, carboxyl, sulfonyl, cyano, thiocyanato, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₉)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonyl and(C₁-C₄)haloalkylsulfonyl and, inclusive of substituents, has 2 to 30carbon atoms, preferably 2 to 20 carbon atoms, in particular 2 to 15carbon atoms.

[0140] Here and also in other radicals, heterocyclyl preferably is aheterocyclic radical having 3 to 7, in particular 3 to 6, ring atoms andone hetero atom selected from the group consisting of N, O and S, forexample pyridyl, thienyl, furyl, pyrrolyl, oxiranyl, oxetanyl, oxolanyl(=tetrahydrofuryl), oxanyl, pyrrolidyl, piperidyl, or is a heterocyclicradical having two or three hetero atoms selected from the groupconsisting of pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl,thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl,piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl,isoxazolidinyl, morpholinyl.

[0141] R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹ R¹⁴, R¹⁵, R¹⁶, R¹⁷ independently ofone another are preferably also (C₁-C₆)alkyl, (C₂-C₆)alkenyl or(C₂-C₆)alkynyl, where each of the last-mentioned 3 radicals isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, hydroxyl, cyano, nitro, thiocyanato,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₂-C₄)alkenyloxy,(C₂-C₄)haloalkenyloxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)haloalkylsulfonyl, (C₃-C₆)cycloalkyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, hydroxyl, amino, cyano, thiocyanato, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino and di(C₁-C₄)alkylamino,phenyl and heterocyclyl, where each of the two last-mentioned radicalsis unsubstituted or substituted by one or more radicals selected fromthe group consisting of halogen, hydroxyl, amino, nitro, formyl,carboxyl, sulfonyl, cyano, thiocyanato, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₉)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonyl and(C₁-C₄)haloalkylsulfonyl, and radicals of the formulae R′—C(═Z′)—,R′—C(═Z′)-Z-, R′-Z-C(═Z′)—, R′R″N—C(═Z′)—, R′-Z-C(═Z′)—O—,R′R″N—C(═Z′)-Z-, R′-Z-C(═Z′)—NR″— and R′R″N—C(═Z′)—NR′″—,

[0142] where R′, R″ and R′″ in each case independently of one anotherare hydrogen or, in particular, (C₁-C₄)alkyl, phenyl,phenyl-(C₁-C₄)alkyl, (C₃-C₆)cycloalkyl or(C₃-C₆)cycloalkyl-(C₁-C₄)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, hydroxyl, amino, nitro,formyl, cyano, thiocyanato, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₂-C₄)alkenyl,(C₂-C₄)alkynyl, (C₃-C₆)cycloalkyl and, in the case of cyclic radicals,also (C₁-C₄)alkyl and (C₁-C₄)haloalkyl, and where Z and Z′ independentlyof one another are in each case one oxygen or sulfur atom, and,inclusive of substituents, preferably has 1 to 20 carbon atoms, inparticular 1 to 15 carbon atoms,

[0143] R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹⁴, R¹⁵, R¹⁶, R¹⁷ in each caseindependently of one another are preferably (C₁-C₄)alkyl which isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,(C₁-C₄)alkylsulfonyl, (C₃-C₉)cycloalkyl which is unsubstituted orsubstituted and phenyl which is unsubstituted or substituted by one ormore radicals selected from the group consisting of halogen,(C₁-C₄)alkyl and (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,(C₁-C₄)alkylthio, amino, mono- and di[(C₁-C₄)alkyl]amino,(C₁-C₄)alkanoylamino, benzoylamino, nitro, cyano,[(C₁-C₄)alkyl]carbonyl, formyl, carbamoyl, mono- anddi[(C₁-C₄)alkyl]aminocarbonyl and (C₁-C₄)alkylsulfonyl, and heterocyclylhaving 3 to 6 ring atoms and 1 to 3 hetero ring atoms selected from thegroup consisting of N, O and S, the ring being unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₄)alkyl and oxo, or phenyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfonyl, cyano,thiocyanato, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₃-C₉)cycloalkyl,[(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl, aminocarbonyl,mono(C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulfonyl and (C₁-C₄)haloalkylsulfonyl and, inclusive ofsubstituents, has 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms,in particular 2 to 15 carbon atoms.

[0144] R¹², R¹³ in each case independently of one another are preferablyalso phenyl which is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, hydroxyl, amino,nitro, formyl, carboxyl, sulfo, cyano, thiocyanato, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₉)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonyl and(C₁-C₄)haloalkylsulfonyl and, inclusive of substituents, has 6 to 30carbon atoms, preferably 6 to 20 carbon atoms, in particular 6 to 15carbon atoms.

[0145] R¹², R¹³ in each case independently of one another are preferablyalso (C₃-C₉)cycloalkyl which is unsubstituted or substituted by one ormore radicals selected from the group consisting of halogen, hydroxyl,amino, cyano, thiocyanato, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino and di(C₁-C₄)alkylamino and,inclusive of substituents, has 3 to 30 carbon atoms, preferably 3 to 20carbon atoms, in particular 3 to 15 carbon atoms.

[0146] R¹², R¹³ in each case independently of one another are preferablyalso heterocyclyl which is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, hydroxyl, amino,nitro, formyl, carboxyl, sulfonyl, cyano, thiocyanato, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₉)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonyl and(C₁-C₄)haloalkylsulfonyl and, inclusive of substituents, has 2 to 30carbon atoms, preferably 2 to 20 carbon atoms, in particular 2 to 15carbon atoms.

[0147] Here and also in other radicals, heterocyclyl is preferably aheterocyclic radical having 3 to 7, in particular 3 to 6, ring atoms andone hetero atom selected from the group consisting of N, O and S, forexample pyridyl, thienyl, furyl, pyrrolyl, oxiranyl, oxetanyl, oxolanyl(=tetrahydrofuryl), oxanyl, pyrrolidyl, piperidyl, or is a heterocyclicradical having two or three hetero atoms selected from the groupconsisting of pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl,thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl,piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl,isoxazolidinyl, morpholinyl.

[0148] R¹², R¹³ in each case independently of one another are preferablyalso (C₁-C₆)alkyl, (C₂-C₆)alkenyl or (C₂-C₆)alkynyl, where each of thelast-mentioned 3 radicals is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, hydroxyl, cyano,nitro, thiocyanato, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₂-C₄)alkenyloxy,(C₂-C₄)haloalkenyloxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)haloalkylsulfonyl, (C₃-C₆)cycloalkyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, hydroxyl, amino, cyano, thiocyanato, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino and di(C₁-C₄)alkylamino, orphenyl and heterocyclyl, where each of the two last-mentioned radicalsis unsubstituted or substituted by one or more radicals selected fromthe group consisting of halogen, hydroxyl, amino, nitro, formyl,carboxyl, sulfonyl, cyano, thiocyanato, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₉)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonyl and(C₁-C₄)haloalkylsulfonyl, and radicals of the formulae R′—C(═Z′)—,R′—C(═Z′)-Z-, R′-Z-C(═Z′)—, R′R″N—C(═Z′)—, R′-Z-C(═Z′)—O—,R′R″N—C(=Z′)-Z-, R′-Z-C(═Z′)—NR″— and R′R″N—C(═Z′)—NR′″—,

[0149] where R′, R″ and R′″ in each case independently of one anotherare hydrogen or, in particular, (C₁-C₄)alkyl, phenyl,phenyl-(C₁-C₄)alkyl, (C₃-C₆)cycloalkyl or(C₃-C₆)cycloalkyl-(C₁-C₄)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, hydroxyl, amino, nitro,formyl, cyano, thiocyanato, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₂-C₄)alkenyl,(C₂-C₄)alkynyl, (C₃-C₆)cycloalkyl and, in the case of cyclic radicals,also (C₁-C₄)alkyl and (C₁-C₄)haloalkyl, and where Z and Z′ independentlyof one another are in each case one oxygen or sulfur atom, and,inclusive of substituents, preferably has 1 to 20 carbon atoms, inparticular 1 to 15 carbon atoms.

[0150] R¹², R¹³ in each case independently of one another are preferably(C₁-C₄)alkyl which is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, (C₁-C₄)alkoxy,(C₁-C₄)alkylthio, (C₁-C₄)alkylsulfonyl, (C₃-C₉)cycloalkyl which isunsubstituted or substituted and phenyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₄)alkyl and (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, amino, mono- anddi[(C₁-C₄)alkyl]amino, (C₁-C₄)alkanoylamino, benzoylamino, nitro, cyano,[(C₁-C₄)alkyl]carbonyl, formyl, carbamoyl, mono- anddi-[(C₁-C₄)alkyl]aminocarbonyl and (C₁-C₄)alkylsulfonyl, andheterocyclyl having 3 to 6 ring atoms and 1 to 3 hetero ring atomsselected from the group consisting of N, O and S, where the ring isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)alkyl and oxo, or phenyl which isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl,sulfonyl, cyano, thiocyanato, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₉)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonyl and(C₁-C₄)haloalkylsulfonyl and, inclusive of substituents, has 2 to 30carbon atoms, preferably 2 to 20 carbon atoms, in particular 2 to 15carbon atoms.

[0151] Independently of the radicals R¹, R², R³, L^(o), A¹, A² and(X)_(n), and preferably in combination with preferred meanings of one ormore of these radicals, the following meanings of R⁴ are of particularinterest:

[0152] R⁴ is, for example, a radical of the formula —B¹-D¹, where B¹ andD¹ are preferably as defined further below.

[0153] R⁴ is preferably hydrogen, (C₁-C₄)alkyl, phenyl or(C₃-C₆)cycloalkyl, where each of the 3 last-mentioned radicals isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl,sulfonyl, cyano, thiocyanato, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,(C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino,di(C₁-C₄)alkylamino, (C₃-C₉)cycloalkyl, [(C₁-C₄)alkyl]carbonyl,[(C₁-C₄)alkoxy]carbonyl, aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl and, in the case of cyclic radicals, also(C₁-C₄)alkyl and (C₁-C₄)haloalkyl, or formyl, [(C₁-C₄)alkyl]carbonyl,[(C₁-C₄)alkoxy]carbonyl, aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl ordi(C₁-C₄)alkylaminocarbonyl; in particular hydrogen, methyl, ethyl,n-propyl or isopropyl; especially preferably hydrogen.

[0154] Independently of the radicals R¹ to R⁴, A¹, A² and (X)_(n), andpreferably in combination with preferred meanings of one or more ofthese radicals, the following meanings of L^(O) are of particularinterest:

[0155] L^(o) is a direct bond or oxygen.

[0156] Independently of the radicals R¹ to R⁴, L^(o), A² and (X)_(n) andpreferably in combination with preferred meanings of one or more ofthese radicals, the following meanings of A¹ are of particular interest:

[0157] A¹ is, for example, straight-chain alkylene having 1 to 5 carbonatoms or straight-chain alkenylene or alkynylene having in each case 2to 5 carbon atoms, where each of the three last-mentioned diradicals isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, nitro, cyano, thiocyanato and a radical ofthe formula —B²-D², in which

[0158] B² is a direct bond or a divalent group of the formulae —O—,—SO₂—, —CO—, —O—CO—, —NR^(O)—, —NR^(O)—CO—, —CO—NR^(O)—, —O—CO—NR^(O)—or —NR^(O)—CO—O—, in which

[0159] R^(O) independently of one another are in each case hydrogen,(C₁-C₄)alkyl, phenyl, phenyl-(C₁-C₄)alkyl, (C₃-C₆)cycloalkyl or(C₃-C₆)cycloalkyl-(C₁-C₄)alkyl, where each of the last-mentioned 5radicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, hydroxyl, amino, nitro,formyl, carboxyl, sulfonyl, cyano, thiocyanato, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₃-C₉)cycloalkyl,[(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl, aminocarbonyl,mono(C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfonyl and, in the case ofcyclic radicals, also (C₁-C₄)alkyl and (C₁-C₄)haloalkyl.

[0160] A¹ is preferably a radical of the formula

[0161] —CH₂—, —CH₂CH₂—, —CH₂CH₂CH₂—, —CH₂CH₂CH₂CH₂— or—CH₂CH₂CH₂CH₂CH₂—, which radical is unsubstituted. Also preferred is oneof the above radicals which is substituted by one or more of theabovementioned radicals —B²-D². A¹ is especially preferably a radical ofthe formula —CH₂CH₂— or —CH₂CH₂CH₂—, which radical is unsubstituted orsubstituted by one or two radicals of the formula hydroxyl, (C₁-C₄)alkylor (C₁-C₄)alkoxy.

[0162] Independently of the radicals R¹ to R⁴, L^(o), A¹ and (X)_(n) andpreferably in combination with preferred meanings of one or more ofthese radicals, the following meanings of A² are of particular interest:

[0163] A² is preferably

[0164] a direct bond or a group of the formula —CH₂—, —CH₂CH₂—,—CH₂CH₂CH₂— or —CH₂CH₂CH₂CH₂—, where each of the 4 last-mentioneddiradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, nitro, cyano, thiocyanatoand radicals of the formula —B³-D³, or a divalent radical of the formulaV¹, V², V³, V⁴ or V⁵,

—CR^(a)R^(b)—W*—CR^(c)R^(d)—  (V¹)

CR^(a)R^(b)—W*—CR^(c)R^(d)—CR^(e)R^(f)—  (V²)

—CR^(a)R^(b)—CR^(c)R^(d)—W*—CR^(e)R^(f)—  (V³)

—CR^(a)R^(b)—CR^(c)R^(d)—W*—  (V4)

CR^(a)R^(b)—W*—  (V⁵)

[0165] where each of the radicals R^(a) to R^(f) in each caseindependently of one other is hydrogen, halogen, nitro, cyano,thiocyanato or a radical of the formula —B⁴-D⁴,

[0166] W* is in each case O, S or a group of the formula N(B⁵-D⁵), andB³, B⁴, B⁵, D³, D⁴ and D⁵ are as defined below.

[0167] A² is especially preferably a direct bond or a group of theformula

[0168] —CH₂—, —CH₂CH₂—, —CH₂CH₂CH₂—, —CH₂CH₂CH₂CH₂, —CH₂O—CH₂—,—CH₂—O—CH₂—CH₂—, —CH₂—CH₂—O—CH₂—, —CH₂—S—CH₂—, —CH₂—S—CH₂—CH₂—,—CH₂—CH₂—S—CH₂—, —CH₂NH—CH₂—, —CH₂—NH—CH₂—CH₂—, —CH₂—CH₂—NH—CH₂—,—CH₂—N(CH₃)—CH₂—, —CH₂—N(CH₃)CH₂CH₂ or —CH₂—CH₂—N(CH₃)—CH₂—.

[0169] B¹ and B⁵ are preferably in each case independently of oneanother a direct bond a divalent group of the formulae —C(═Z*)—,—C(═Z*)-Z**-, —C(═Z*)—NH— or —C(═Z*)—NR*—, where Z*=O or S, Z**=O or Sand R*=(C₁-C₄)alkyl, phenyl, phenyl-(C₁-C₄)alkyl, (C₃-C₆)cycloalkyl or(C₃-C₆)cycloalkyl(C₁-C₄)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted, preferably unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfo, cyano,thiocyanato, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₉)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl and, in the case of cyclic radicals, also(C₁-C₄)alkyl and (C₁-C₄)haloalkyl.

[0170] B¹ and B⁵ are also preferably independently of another a directbond or a divalent group of the formulae —C(═Z*)—, —C(═Z*)-Z**-,—C(═Z*)—NH— or —C(═Z*)—NR*—, where Z*=O or S, Z**=O or S and

[0171] R*=(C₁-C₄)alkyl, phenyl, phenyl-(C₁-C₄)alkyl, (C₃-C₆)cycloalkylor (C₃-C₆)cycloalkyl-(C₁-C₄)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, hydroxyl, amino, formyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₃-C₉)cycloalkyl,[(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl, aminocarbonyl,mono(C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl and, in thecase of cyclic radicals, also (C₁-C₄)alkyl and (C₁-C₄)haloalkyl, inparticular R*=(C₁-C₄)alkyl or (C₃-C₆)cycloalkyl or in particularR*=phenyl or phenyl-(C₁-C₄)alkyl, where each of the two last-mentionedradicals is unsubstituted or substituted in the phenyl moiety or by oneor more radicals selected from the group consisting of halogen,(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy or (C₁-C₄)haloalkoxy.

[0172] B², B³ and B⁴ are preferably in each case independently of oneanother a direct bond or a divalent group of the formulae —O—,—S(O)_(p)—, —S(O)_(p)—O—, —O—S(O)_(p)—, —CO—, —O—CO—, —CO—O—, —S—CO—,—CO—S—, —S—CS—, —CS—S—, —O—CO—O—, —NR^(O)—, —O—NR^(O)—, —NR^(O)—O—,—NR^(O)—CO—, —CO—NR^(O)—, —O—CO—NR^(O)— or —NR^(O)—CO—O—, where p is theinteger 0, 1 or 2 and R^(O)=hydrogen, (C₁-C₄)alkyl, phenyl,phenyl-(C₁-C₄)alkyl, (C₃-C₆)cycloalkyl or(C₃-C₆)cycloalkyl-(C₁-C₄)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, hydroxyl, amino, nitro,formyl, carboxyl, sulfo, cyano, thiocyanato, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₃-C₉)cycloalkyl,[(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl, aminocarbonyl,mono(C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfonyl and, in the case ofcyclic radicals, also (C₁-C₄)alkyl and (C₁-C₄)haloalkyl, and inparticular R^(O)=hydrogen, (C₁-C₄)alkyl or (C₃-C₆)cycloalkyl or inparticular R^(O)=phenyl or phenyl-(C₁-C₄)alkyl, where each of the twolast-mentioned radicals is unsubstituted or substituted in the phenylmoiety by one or more radicals selected from the group consisting ofhalogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy or(C₁-C₄)haloalkoxy.

[0173] B², B³ and B⁴ are also preferably independently of one another

[0174] a direct bond or a

[0175] divalent group of the formulae —O—, —S(O)_(p)—, —CO—, —O—CO—,—CO—O—, —S—CO—, —CO—S—, —NR^(O)—, —NR^(O)—CO—, —CO—NR^(O)—,—O—CO—NR^(O)— or —NR^(O)—CO—O—, where p is the integer 0, 1 or 2, inparticular 0 or 2, and R^(O) has the abovementioned meaning, veryespecially H or (C₁-C₄)alkyl.

[0176] D¹, D², D³, D⁴ and D⁵ preferably independently of one another arehydrogen, (C₁-C₆)alkyl, phenyl, phenyl-(C₁-C₄)alkyl, (C₃-C₆)cycloalkylor (C₃-C₆)cycloalkyl-(C₁-C₆)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted, preferably unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfo, cyano,thiocyanato, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₉)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl and, in the case of cyclic radicals, also(C₁-C₄)alkyl and (C₁-C₄)haloalkyl.

[0177] D¹, D², D³, D⁴ and D⁵ also preferably independently of oneanother are (C₁-C₄)alkyl, phenyl, phenyl-(C₁-C₄)alkyl, (C₃-C₆)cycloalkylor (C₃-C₆)cycloalkyl-(C₁-C₄)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, hydroxyl, amino, formyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₃-C₉)cycloalkyl,[(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl, aminocarbonyl,mono(C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl and, in thecase of cyclic radicals, also (C₁-C₄)alkyl and (C₁-C₄)haloalkyl, and, inparticular, they are (C₁-C₄)alkyl or (C₃-C₆)cycloalkyl or phenyl orphenyl-(C₁-C₄)alkyl, where each of the two last-mentioned radicals isunsubstituted or substituted in the phenyl moiety by one or moreradicals selected from the group consisting of halogen, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy or (C₁-C₄)haloalkoxy.

[0178] Independently of the radicals R¹ to R⁴, L^(o), A¹ and A² andpreferably in combination with preferred meanings of one or more ofthese radicals, the following meanings of (X)_(n) are of particularinterest:

[0179] (X)_(n) is n substituents X, where X preferably in each caseindependently of one another are halogen, hydroxyl, amino, nitro,formyl, carboxyl, cyano, thiocyanato, aminocarbonyl or (C₁-C₄)alkyl,(C₁-C₄)alkoxy, (C₁-C₄)alkylthio, mono(C₁-C₄)alkylamino,di(C₁-C₄)alkylamino, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl,[(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,mono(C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,N-(C₁-C₆)alkanoylamino or N-(C₁-C₄)alkanoyl-N-(C₁-C₄)alkylamino,

[0180] where each of the last-mentioned 13 radicals is unsubstituted orsubstituted, preferably unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, hydroxyl, amino,cyano, thiocyanato, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkylamino, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, phenyl, phenoxy, phenylthio,phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio andheterocyclylamino,

[0181] where each of the last-mentioned 8 radicals is unsubstituted orhas one or more substituents selected from the group consisting ofhalogen, nitro, cyano, (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, formyl, (C₁-C₄)alkylcarbonyl and(C₁-C₄)alkoxycarbonyl,

[0182]  or (C₃-C₉)cycloalkyl, phenyl, phenoxy, phenylthio,phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio orheterocyclylamino,

[0183] where each of the last-mentioned 9 radicals is unsubstituted orsubstituted, preferably unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, hydroxyl, amino,nitro, formyl, carboxyl, cyano, thiocyanato, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₆)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl anddi(C₁-C₄)alkylaminocarbonyl,

[0184]  or two adjacent radicals X together are a fused cycle having 4to 6 ring atoms which is carbocyclic or contains hetero ring atomsselected from the group consisting of O, S and N and which isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)alkyl and oxo.

[0185] In this context, n is preferably 0, 1, 2 or 3, in particular 0, 1or 2.

[0186] (X)_(n) is also preferably n substituents X, where X in each caseindependently of one another are halogen, hydroxyl, amino, nitro,formyl, carboxyl, cyano, thiocyanato, (C₁-C₄)alkyl, cyano-(C₁-C₄)alkyl,(C₁-C₄)alkoxy, (C₁-C₄)alkylamino, di[(C₁-C₄)alkyl]amino,halo(C₁-C₄)alkyl, hydroxyl(C₁-C₄)alkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,halo(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)alkylthio, halo(C₁-C₄)alkylthio,(C₂-C₆)alkenyl, halo(C₂-C₆)alkenyl, (C₂-C₆)alkynyl, halo(C₂-C₆)alkynyl,(C₁-C₄)alkylamino-(C₁-C₄)alkyl, di[(C₁-C₄)alkyl]amino-(C₁-C₄)alkyl,(C₃-C₆)cycloalkylamino-(C₁-C₄)alkyl, (C₃-C₉)cycloalkyl,heterocyclyl-(C₁-C₄)alkyl having 3 to 9 ring members, where the cyclicgroups in the last-mentioned 3 radicals are unsubstituted or substitutedby one or more radicals, preferably up to three radicals, selected fromthe group consisting of (C₁-C₄)alkyl, halogen and cyano, or phenyl,phenoxy, phenylcarbonyl, phenylcarbonyl-(C₁-C₄)alkyl,(C₁-C₄)alkoxy-carbonyl-(C₁-C₄)alkyl,(C₁-C₄)alkylaminocarbonyl-(C₁-C₄)alkyl, (C₁-C₄)alkyl-carbonyl,(C₁-C₄)alkoxycarbonyl, aminocarbonyl, (C₁-C₄)alkylaminocarbonyl,phenoxy-(C₁-C₄)alkyl, phenyl-(C₁-C₄)alkyl, heterocyclyl,heterocyclylamino, heterocyclyloxy, heterocyclylthio or one of thelast-mentioned 16 radicals which is substituted in the acyclic moietyor, preferably in the cyclic moiety by one or more radicals selectedfrom the group consisting of halogen, nitro, cyano, (C₁-C₄)alkyl,(C₁-C₄)alkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy,formyl, (C₁-C₄)alkylcarbonyl, (C₁-C₄)alkoxycarbonyl, (C₁-C₄)alkoxy,where heterocyclyl in the radicals contains in each case 3 to 9 ringatoms and 1 to 3 hetero ring atoms selected from the group consisting ofN, O and S, or two adjacent radicals X together are a fused cycle having4 to 6 ring atoms which is carbocyclic or contains hetero ring atomsselected from the group consisting of O, S and N and which isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)alkyl and oxo.

[0187] (X)_(n) is especially preferably n substituents X and where X ineach case independently of one another are halogen, OH, NO₂, CN,SCN(C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₁-C₄)alkylcarbonyl or(C₁-C₄)alkyloxycarbonyl, where the last-mentioned four radicals areunsubstituted or substituted by halogen or (C₁-C₄)alkoxy, and veryespecially preferably n substituents X and where X in each caseindependently of one another are halogen, hydroxyl, (C₁-C₄)alkyl or(C₁-C₄)alkoxy.

[0188] Heterocyclyl in the radicals mentioned hereinabove or furtherbelow are, independently of one another preferably a heterocyclicradical having 3 to 7 ring atoms selected from the group consisting ofN, O and S, preferably a heteroaromatic radical selected from the groupconsisting of pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl,thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, furyl, pyrrolyl,pyrazolyl, imidazolyl and triazolyl or a partially or fully hydrogenatedheterocyclic radical selected from the group consisting of oxiranyl,oxetanyl, oxolanyl (=tetrahydrofuryl), oxanyl, pyrrolidyl, piperidyl,piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl,isoxazolidinyl and morpholinyl.

[0189] Especially preferably, heterocyclyl is a heterocyclic radicalhaving 3 to 6 ring atoms and one (1) hetero atom selected from the groupconsisting of N, O and S, in particular a heteroaromatic radical having5 or 6 ring atoms or a saturated or partially unsaturated heterocyclic(not heteroaromatic) radical having 3 to 6 ring atoms.

[0190] Moreover, heterocyclyl is preferably a heterocyclic radicalhaving 5 or 6 ring atoms and 2 or 3 hetero atoms selected from the groupconsisting of N, O and S, in particular pyrimidinyl, pyridazinyl,pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl,pyrazolyl, imidazolyl, triazolyl or piperazinyl, dioxolanyl, oxazolinyl,isoxazolinyl, oxazolidinyl, isoxazolidinyl or morpholinyl.

[0191] The composite group -A²-R² is preferably cyclopropyl (hereinbelowalso “c-Pr”), CH₂-c-Pr, —(CH₂)₂-Pr, cyclobutyl (hereinbelow also“c-Bu”), CH₂-c-Bu; (CH₂)₂-c-Bu, oxiranyl, oxiranylmethyl or2-(oxiranyl)-eth-1-yl.

[0192] Subject matter of the present invention are also processes forthe preparation of compounds of the formula (I) and their salts

[0193] where A¹, A², L⁰, R¹, R², R³, R⁴, X and n are as definedhereinabove, wherein

[0194] a) in the event that R³ in formula (I) is a group of the formula-L¹-N═C(U¹)(U³), where L¹, U¹ and U³ are as defined further above underR³, a compound of the formula (II)

[0195]  where A¹, A², L⁰, L¹, R¹, R², R⁴, X and n are as defined informula (I) is reacted with a compound of the formula (III)

[0196]  where U¹ and U³ are as defined in formula (I) and R¹⁸ and R¹⁹independently of one another are unsubstituted or substituted alkylhaving up to 12 carbon atoms, preferably (C₁-C₄)alkyl, or jointly linkedare an alkylene group having 2 to 4 carbon atoms, or

[0197] b) in the event that R³ in formula (I) is a group of the formulaL¹-NG¹-C(U²)═N—U⁴ where L¹, G¹, U² and U⁴ are as defined further aboveunder R³, a compound of the formula (IV)

[0198]  where A¹, A², L⁰, L¹, R¹, R², R⁴, G¹, X and n are as defined informula (I) is reacted with a compound of the formula (V)

[0199]  where U² and U⁴ are as defined in formula (I) and R¹⁸ is asdefined in formula (III), or

[0200] c) in the event that R³ in formula (I) is a group of the formula-L¹-N═C(U¹)(U³) where U³═NG¹⁸NG¹⁹G²⁰, NG²¹OG²² or NG²³SG²⁴ and L¹, U¹,G¹⁸, G¹⁹, G²⁰, G²¹, G²², G²³, G²⁴ are as defined further above under R³,a compound of the formula (VI)

[0201]  where A¹, A², L⁰, L¹, R¹, R², R⁴, U¹, X and n are as defined informula (I) and R⁶ and R⁷ are as defined further above, is reacted witha compound of the formula (VII) or its acid adducts

H—U³  (VII)

[0202]  where U³ is as defined in formula (I), or

[0203] d) in the event that R³ in formula (I) is a group of the formula-L¹-N═C(U¹)(U³) where U¹=R¹⁴ and U³=R¹⁵ and L¹, R¹⁴ and R¹⁵ are asdefined further above, a compound of the formula (II) is reacted inaccordance with variant a) with an aldehyde or ketone of the formula(VIII)

U¹—CO—U³  (VIII)

[0204] where U¹ and U³ are as defined in formula (I).

[0205] The substituted aminotriazines of the formula (II) used in theprocess according to the invention, variant a) for the preparation ofcompounds of the formula (I) are known and/or can be prepared byprocesses known per se (cf. WO-A-9965882). The starting materials of theformula (III) are known (cf. Chem. Ber. 89, 2060 (1956), Liebigs Anm.Chem. 641, 1 (1961), Chem. Ber. 96, 1350 (1963)) or can be preparedanalogously to the known processes.

[0206] If appropriate, variant a) of the process according to theinvention for the preparation of compounds of the formula (I) is carriedout using a diluent. Suitable diluents for this purpose are, mainly,inert organic solvents. These include, in particular, aliphatic,alicyclic or aromatic, optionally halogenated hydrocarbons such as, forexample, benzine, benzene, toluene, xylene, chlorobenzene,dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane,chloroform, carbon tetrachloride; ethers such as diethyl ether,diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethylether or ethylene glycol diethyl ether; ketones such as acetone,butanone or methyl isobutyl ketone; nitriles such as acetonitrile,propionitrile or butyronitrile; amides such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide; esters such as methyl acetate or ethylacetate, sulfoxides such as dimethyl sulfoxide, alcohols such asmethanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether,ethylene glycol monoethyl ether, diethylene glycol monomethyl ether ordiethylene glycol monoethyl ether.

[0207] When carrying out the process according to the invention, thereaction temperatures can be varied within a substantial range. Ingeneral, the process is carried out at temperatures between 0° C. and150° C., preferably between 10° C. and 120° C.

[0208] As a rule, the process according to the invention is carried outunder atmospheric pressure. However, it is also possible to carry outthe process according to the invention under elevated or reducedpressure, in general between 0.1 bar and 10 bar.

[0209] To carry out the process according to the invention, the startingmaterials are employed in, for example, equimolar amounts. However, itis also possible to use one of the components in a more or less largeexcess, for example when the component of which substoichiometricamounts are used is to complete its reaction quickly in order to reduceside reactions. The reaction is carried out for example in a suitablediluent in the presence of a reaction auxiliary, the reaction mixturegenerally being mixed, for example stirred, for several hours at thetemperature required. Work-up can be carried out by customary methods(cf. also the Preparation Examples).

[0210] The substituted aminotriazines of the formula (IV) used invariant b) of the process according to the invention for the preparationof compounds of the formula (I) are known and/or can be prepared byprocesses known per se (cf. WO-A-9965882).

[0211] The compounds of the formula (V) are known, for example, from J.Org. Chem. 30, pp. 2531-2533 (1965).

[0212] If appropriate, variant b) of the process according to theinvention for the preparation of compounds of the formula (I) is carriedout using a diluent. Suitable diluents for this purpose are, mainly,inert organic solvents. These include, in particular, aliphatic,alicyclic or aromatic, optionally halogenated hydrocarbons such as, forexample, benzine, benzene, toluene, xylene, chlorobenzene,dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane,chloroform, carbon tetrachloride; ethers such as diethyl ether,diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethylether or ethylene glycol diethyl ether; ketones such as acetone,butanone or methyl isobutyl ketone; nitriles such as acetonitrile,propionitrile or butyronitrile; amides such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide; esters such as methyl acetate or ethylacetate, sulfoxides such as dimethyl sulfoxide, alcohols such asmethanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether,ethylene glycol monoethyl ether, diethylene glycol monomethyl ether ordiethylene glycol monoethyl ether.

[0213] When carrying out the process according to the invention, thereaction temperatures can be varied within a substantial range. Ingeneral, the process is carried out at temperatures between 0° C. and150° C., preferably between 10° C. and 120° C.

[0214] Variant b) of the process according to the invention is carriedout in a simple manner, for example under atmospheric pressure. However,it is also possible to carry out the process according to the inventionunder elevated or reduced pressure, preferably between 0.1 bar and 10bar.

[0215] To carry out variant b) of the process, the starting materialscan be employed in equimolar amounts. However, it is also possible touse one of the components in a more or less large excess. The reactionis preferably carried out in a suitable diluent in the presence of areaction auxiliary. As a rule, the reaction proceeds to completion inthe course of several hours with stirring at the temperature required.Work-up can be carried out by customary methods (cf. the PreparationExamples).

[0216] To prepare the compounds (I) following variant c), compounds ofthe formula (VI) are employed. Compounds of the formula (VI) can beprepared from amino compounds of the formula (II) following variant a),for example by reaction with compounds of the formula (III) where U¹,R¹⁸, R¹⁹ are as defined in formula (III) and U³=NR⁶R⁷, where R⁶ and R⁷are as defined in formula (I) (=Compounds (IIIa)). The compounds of theformula (VII) are known or can be prepared by known methods. Ifappropriate, variant c) of the process according to the invention iscarried out using a diluent. Suitable diluents for this purpose are,mainly, inert organic solvents. These include, in particular, aliphatic,alicyclic or aromatic, optionally halogenated hydrocarbons such as, forexample, benzine, benzene, toluene, xylene, chlorobenzene,dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane,chloroform, carbon tetrachloride; ethers such as diethyl ether,diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethylether or ethylene glycol diethyl ether; ketones such as acetone,butanone or methyl isobutyl ketone; nitriles such as acetonitrile,propionitrile or butyronitrile; amides such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide; esters such as methyl acetate or ethylacetate, sulfoxides such as dimethyl sulfoxide, alcohols such asmethanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether,ethylene glycol monoethyl ether, diethylene glycol monomethyl ether ordiethylene glycol monoethyl ether.

[0217] The other reaction conditions, such as ranges for reactiontemperatures, pressure conditions, proportions and the like are similarto those in variants a) and b).

[0218] If appropriate, variant d) of the process according to theinvention is carried out using a diluent. Suitable diluents for thispurpose are, mainly, inert organic solvents. These include, inparticular, aliphatic, alicyclic or aromatic, optionally halogenatedhydrocarbons such as, for example, benzine, benzene, toluene, xylene,chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane,dichloromethane, chloroform, carbon tetrachloride; ethers such asdiethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, ethyleneglycol dimethyl ether or ethylene glycol diethyl ether; ketones such asacetone, butanone or methyl isobutyl ketone; nitriles such asacetonitrile, propionitrile or butyronitrile; amides such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide,N-methylpyrrolidone or hexamethylphosphoric triamide; esters such asmethyl acetate or ethyl acetate; sulfoxides such as dimethyl sulfoxide,alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycolmonomethyl ether, ethylene glycol monoethyl ether, diethylene glycolmonomethyl ether or diethylene glycol monoethyl ether.

[0219] The compounds of the formula (VIII) which are employed in variantd) of the process are known or can be prepared by known methods.

[0220] The other reaction conditions, such as ranges for reactiontemperatures, pressure conditions, proportions and the like are similarto those in variants a) and b) and c).

[0221] The water which is liberated during the reaction (reaction water)can be removed for example by azeotropic distillation, water-bindingsalts or molecular sieves.

[0222] The respective starting compounds of the formulae (II) to (VIII)are known or can be prepared by the abovementioned methods oranalogously to known processes.

[0223] The following acids are suitable for preparing the acid additionsalts of the compounds of the formula (I): hydrohalic acids such ashydrochloric acid or hydrobromic acid, furthermore phosphoric acid,nitric acid, sulfuric acid, mono- or bifunctional carboxylic acids andhydroxycarboxylic acids such as acetic acid, maleic acid, succinic acid,fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid orlactic acid, and also sulfonic acids such as p-toluenesulfonic acid or1,5-naphthalenedisulfonic acid. The acid addition compounds of theformula (I) can be obtained simply by the customary salt formationmethods, for example by dissolving a compound of the formula (I) in asuitable organic solvent such as, for example, methanol, acetone,methylene chloride or benzine, and adding the acid at temperatures offrom 0 to 100° C., and they can be isolated in a known fashion, forexample by filtration, and, if appropriate, purified by washing with aninert organic solvent.

[0224] The base addition salts of the compounds of the formula (I) arepreferably prepared in inert polar solvents such as, for example, water,methanol or acetone at temperature from 0 to 100° C. Examples ofsuitable bases for preparing the salts according to the invention arealkali metal carbonates, such as potassium carbonate, alkali metal andalkaline earth metal hydroxides, for example NaOH or KOH, alkali metaland alkaline earth metal hydrides, for example NaH, alkali metal andalkaline earth metal alkoxides, for example sodium methoxide, potassiumtert-butoxide, or ammonia or ethanolamine. Quaternary ammonium salts canbe obtained, for example, by salt exchange or condensation withquaternary ammonium salts of the formula [NRR′R″R′″]⁺X⁻ where R, R′, R″and R′″ independently of one another are (C₁-C₄)alkyl, phenyl or benzyland X is an anion, for example Cl⁻ or OH⁻.

[0225] The “inert solvents” which the above process variants refer toare to be understood as meaning in each case solvents which are inertunder the reaction conditions in question, but which need not be inertunder any desired reaction conditions.

[0226] A collection of compounds (I) which can be synthesized by theabove-mentioned processes can additionally be prepared in parallelizedfashion, which can be effected manually, partly automated or fullyautomated. In this context, it is possible to automate the procedure ofthe reaction, work-up or purification of the products or intermediates.In total, this is to be understood as meaning a procedure which isdescribed, for example, by S. H. DeWitt in “Annual Reports inCombinatorial Chemistry and Molecular Diversity: Automated Synthesis”,Volume 1, published by Escom, 1997, pages 69 to 77.

[0227] For carrying out the reaction and work-up in parallelizedfashion, a series of commercially available apparatuses can be used asthey are available from, for example, Stem Corporation, Woodrolfe Road,Tollesbury, Essex, CM9 8SE, England or H+P Labortechnik GmbH,Bruckmannring 28,85764 Oberschleiβheim, Germany. To carry out theparallelized purification of compounds (I) or of intermediates obtainedduring the preparation, there are available, inter alia, chromatographicequipment, for example from ISCO, Inc., 4700 Superior Street, Lincoln,Nebr. 68504, USA. The equipment mentioned makes possible a modularprocedure, where the individual steps are automated, but manualoperation has to be carried out between the steps. This can becircumvented by employing partly or fully integrated automation systems,in which the automation modules in question are operated by, forexample, robots. Such automation systems can be obtained from, forexample, Zymark Corporation, Zymark Center, Hopkinton, Mass. 01748, USA.

[0228] In addition to the above-described methods, compounds (I) can beprepared in full or partly by solid-phase supported methods. To thisend, individual intermediates or all intermediates of the synthesis orof a synthesis adapted to the procedure in question are bound to asynthesis resin. Solid-phase supported synthetic methods are describedextensively in the specialist literature, for example: Barry A. Bunin in“The Combinatorial Index”, published by Academic Press, 1998.

[0229] The use of solid-phase supported synthesis methods permits aseries of protocols known from the literature which, in turn, can becarried out manually or in an automated fashion. For example, the“teabag method” (Houghten, U.S. Pat. No. 4,631,211; Houghten et al.,Proc. Natl. Acad. Sci., 1985, 82, 5131-5135) can be partly automatedwith products of IRORI, 11149 North Torrey Pines Road, La Jolla, Calif.92037, USA. Solid-phase supported parallel synthesis can be automatedsuccessfully for example using equipment by Argonaut Technologies, Inc.,887 Industrial Road, San Carlos, Calif. 94070, USA or MultiSynTech GmbH,Wullener Feld 4, 58454 Witten, Germany.

[0230] The preparation in accordance with the processes described hereinyields compounds (I) in the form of substance collections or substancelibraries. Subject matter of the present invention are therefore alsolibraries of the compounds (I) which contain at least two compounds (I),and of their precursors.

[0231] The compounds of the formula (I) according to the invention andtheir salts, hereinbelow together termed compounds of the formula (I)(according to the invention) have an excellent herbicidal activityagainst a broad spectrum of economically important mono- anddicotyledonous harmful plants. The active substances also actefficiently on perennial weeds which produce shoots from rhizomes, rootstocks or other perennial organs and are difficult to control. In thiscontext, it is unimportant whether the substances are applied beforesowing, preemergence or postemergence.

[0232] Specifically, some representatives of the mono- anddicotyledonous weed flora which can be controlled by the compoundsaccording to the invention may be mentioned by way of example, without arestriction to certain species being intended to take place as a resultof the mention.

[0233] Amongst the monocotyledonous weed species, those on which theactive substances act efficiently are, for example, Agrostis,Alopecurus, Apera, Avena, Brachicaria, Bromus, Dactyloctenium,Digitaria, Echinochloa, Eleocharis, Eleusine, Festuca, Fimbristylis,lschaemum, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa,Sagittaria, Scirpus, Setaria, Sphenoclea and Cyperus species from theannual group and, amongst the perennial species, Agropyron, Cynodon,Imperata and Sorghum and also perennial Cyperus species. In the case ofdicotyledonous weed species, the spectrum of action extends to speciessuch as, for example, Galium, Viola, Veronica, Lamium, Stellaria,Amaranthus, Sinapis, lpomoea, Matricaria, Abutilon and Sida amongst theannuals and Convolvulus, Cirsium, Rumex and Artemisia in the case of theperennial weeds. Herbicidal action is also achieved in the case ofdicotyledonous harmful plants such as

[0234] Ambrosia, Anthemis, Carduus, Centaurea, Chenopodium, Cirsium,Convolvulus, Datura, Emex, Galeopsis, Galinsoga, Lepidium, Lindemia,Papaver, Portlaca, Polygonum, Ranunculus, Rorippa, Rotala, Seneceio,Sesbania, Solanum, Sonchus, Taraxacum, Trifolium, Urtica and Xanthium.

[0235] Harmful plants occurring under the specific cultivationconditions of rice, such as, for example, Sagittaria, Alisma,Eleocharis, Scirpus and Cyperus, are also outstandingly well controlledby the active substances according to the invention.

[0236] If the compounds according to the invention are applied to thesoil surface before germination, then the weed seedlings are eitherprevented completely from emerging or the weeds grow until they havereached the cotyledon stage, but then their growth stops and theyfinally die completely after three to four weeks have elapsed. When theactive substances are applied postemergence to the green parts of theplants, growth stops equally drastically a very short time aftertreatment and the weed plants remain at the stage of growth at the timeof application, or they die completely after a certain time, so that inthis manner competition by the weeds, which is harmful to the cropplants, is eliminated at a very early stage and in a sustained manner.

[0237] Although the compounds according to the invention have anexcellent herbicidal activity against mono- and dicotyledonous weeds,crop plants of economically important crops such as, for example, wheat,barley, rye, triticale, rice, maize, sugar beet, cotton and soybeans,are damaged only to an insignificant extent or not at all. For thesereasons, the present compounds are very highly suitable for theselective control of undesired vegetation in stands of agriculturallyuseful plants or in stands of ornamental plants.

[0238] In addition, the substances according to the invention haveoutstanding growth-regulatory properties in crop plants. They engage inthe plants' metabolism in a regulatory fashion and can thus be employedfor influencing plant constituents in a targeted fashion and forfacilitating harvesting, such as, for example, by triggering desiccationand stunted growth. Moreover, they are also suitable for generallycontrolling and inhibiting undesired vegetative growth withoutsimultaneously killing the plants. Inhibiting vegetative growth plays animportant role in many monocotyledonous and dicotyledonous crops sincelodging can be reduced, or prevented completely, hereby.

[0239] On account of their herbicidal and plant growth-regulatoryproperties, the active substances can also be employed for the controlof harmful plants in crops of known genetically modified plants orgenetically modified plants yet to be developed. As a rule, thetransgenic plants are distinguished by particularly advantageousproperties, for example by resistances to certain pesticides, especiallycertain herbicides, resistances to plant diseases or pathogens of plantdiseases such as certain insects or microorganisms such as fungi,bacteria or viruses. Other particular properties relate, for example, tothe harvested material with respect to quantity, quality, storability,composition and specific constituents. Thus, transgenic plants having anincreased starch content or where the quality of the starch is alteredor those having a different fatty acid composition of the harvestedmaterial are known.

[0240] The compounds of the formula (I) according to the invention ortheir salts are preferably used in economically important transgeniccrops of useful and ornamental plants, e.g. of cereals such as wheat,barley, rye, oats, sorghum and millet, rice, cassaya and corn oralternatively crops of sugar beet, cotton, soybeans, oilseed rape,potatoes, tomatoes, peas and other types of vegetables.

[0241] The compounds of the formula (I) can preferably be employed asherbicides in useful plant crops which are resistant, or have been maderesistant, by recombinant methods, to the phytotoxic effects of theherbicides.

[0242] Traditional ways of generating novel plants which have modifiedcharacteristics in comparison with existing plants consist, for example,in traditional breeding methods and the generation of mutants.Alternatively, novel plants with modified characteristics can begenerated using recombinant procedures (see, for example, EP-A-0221044,EP-A-0131624). For example, a number of cases have been described of

[0243] recombinant modifications of crop plants for the purpose ofmodifying the starch synthesized in the plants (e.g. WO 92/11376, WO92/14827, WO 91/19806),

[0244] transgenic crop plants which are resistant to certain herbicidesof the glufosinate type (cf., for example, EP-A-0242236, EP-A-242246) orof the glyphosate type (WO 92/00377) or of the sulfonylurea type(EP-A-0257993, U.S. Pat. No. 5,013,659),

[0245] transgenic crop plants, for example cotton, with the capabilityof producing Bacillus thuringiensis toxins (Bt toxins) which make theplants resistant to certain pests (EP-A-0142924, EP-A-0193259),

[0246] transgenic crop plants having a modified fatty acid composition(WO 91/13972).

[0247] Numerous molecular biology techniques using which noveltransgenic plants having modified properties can be produced are knownin principle; see, for example, Sambrook et al., 1989, MolecularCloning, A Laboratory Manual, 2nd Ed., Cold Spring Harbor LaboratoryPress, Cold Spring Harbor, N.Y.; or Winnacker “Gene und Klone” [Genesand Clones], VCH Weinheim, 2nd Edition, 1996 or Christou, “Trends inPlant Science” 1 (1996)423-431).

[0248] For recombinant manipulations of this type, nucleic acidmolecules can be introduced into plasmids which allow mutagenesis or asequence modification by means of recombination of DNA sequences. Withthe aid of the above-mentioned standard procedures, it is possible, forexample, to perform base exchanges, to remove subsequences or to addnatural or synthetic sequences. For the connection of the DNA fragmentsto one another, adaptors or linkers can be attached to the fragments.

[0249] For example, plant cells having a reduced activity of a geneproduct can be produced by the expression of at least one correspondingantisense RNA, a sense RNA to achieve a cosuppression effect or theexpression of at least one appropriately constructed ribozyme whichspecifically cleaves transcripts of the abovementioned gene product.

[0250] For this, it is possible to use, on the one hand, DNA moleculeswhich comprise the entire coding sequence of a gene product includingflanking sequences which may be present, and also DNA molecules whichonly comprise parts of the coding sequence, where these parts must belong enough in order to bring about an antisense effect in the cells.The use of DNA sequences which have a high degree of homology to thecoding sequences of a gene product, but are not completely identical, isalso possible.

[0251] When nucleic acid molecules are expressed in plants, thesynthesized protein can be localized in any desired compartment of theplant cell. However, in order to achieve localization in a certaincompartment, it is possible, for example, to link the coding region withDNA sequences which guarantee localization in a certain compartment.Sequences of this type are known to the person skilled in the art (see,for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al.,Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., PlantJ. 1 (1991), 95-106).

[0252] The transgenic plant cells can be regenerated to give intactplants according to known techniques. In principle, the transgenicplants can be plants of any desired plant species, i.e. bothmonocotyledonous and dicotyledonous plants. Transgenic plants are thusobtainable which have modified properties as a result of overexpression,suppression or inhibition of homologous (=natural) genes or genesequences or expression of heterologous (=foreign) genes or genesequences.

[0253] The compounds (I) according to the invention can preferably beemployed in transgenic crops which are resistant to herbicides from thegroup consisting of the sulfonylureas, glufosinate-ammonium orglyphosate-isopropylammonium and analogous active substances.

[0254] When the active substances according to the invention are used intransgenic crops, in addition to the effects against harmful plants tobe observed in other crops, effects often occur which are specific forapplication in the particular transgenic crop, for example a modified orspecifically widened spectrum of weeds which can be controlled, alteredapplication rates which can be employed for application, preferably goodcombining ability with the herbicides to which the transgenic crop isresistant, and an effect on growth and yield of the transgenic cropplants.

[0255] The invention therefore also relates to the use of the compounds(I) according to the invention as herbicides for controlling harmfulplants in transgenic crop plants.

[0256] The use according to the invention for controlling harmful plantsor for regulating the growth of plants also includes the case where theactive substance of the formula (I) or its salt is formed from a prodrugonly after application on the plant, in the plant or in the soil.

[0257] The compounds according to the invention can be used in thecustomary preparations in the form of wettable powders, emulsifiableconcentrates, sprayable solutions, dusting agents or granules. Theinvention therefore also relates to herbicidal and plantgrowth-regulating compositions which contain compounds of the formula(I).

[0258] The compounds of the formula (I) can be formulated in variousways, depending on what biological and/or chemicophysical parameters areprespecified. Examples of suitable formulation possibilities are:wettable powders (WP), water-soluble powders (SP), water-solubleconcentrates, emulsifiable concentrates (EC), emulsions (EW), such asoil-in-water and water-in-oil emulsions, sprayable solutions, suspensionconcentrates (SC), dispersions on an oil or water basis, oil-misciblesolutions, capsule suspensions (CS), dusting agents (DP), dressingagents, granules for broadcasting and soil application, granules (GR) inthe form of microgranules, spray granules, coated granules andadsorption granules, water-dispersible granules (WG), water-solublegranules (SG), ULV formulations, microcapsules and waxes.

[0259] These individual formulation types are known in principle and aredescribed, for example, in: Winnacker-Küchler, “Chemische Technologie”[Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition1986, Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker,N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G.Goodwin Ltd. London.

[0260] The necessary or applicable formulation auxiliaries such as inertmaterials, surfactants, solvents and other additives are also in manycases known and are described, for example, in: Watkins, “Handbook ofInsecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books,Caldwell N.J., H. v. Olphen, “Introduction to Clay Colloid Chemistry”;2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed.,Interscience, N.Y. 1963; McCutcheon's “Detergents and EmulsifiersAnnual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopediaof Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Surface-Active Ethylene OxideAdducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie” [Chemical Technology], Volume 7, C. HauserVerlag Munich, 4th Edition 1986.

[0261] On the basis of these formulations, combinations with otherpesticidally active substances such as, for example, insecticides,acaricides, herbicides, fungicides, and also with safeners, fertilizersand/or growth regulators can also be prepared, e.g. in the form of afinished formulation or as a tank mix.

[0262] Wettable powders are preparations which are uniformly dispersiblein water and which, besides the active compound, also containsurfactants of ionic and/or nonionic type (wetting agents, dispersants),e.g. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols,polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates,alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonates, sodium2,2′-dinaphthylmethane-6,6′-disulfonate, sodiumdibutylnaphthalene-sulfonate or alternatively sodium oleoylmethyltauratein addition to a diluent or inert substance. For preparation of thewettable powders, the herbicidal active substances are finely ground,for example, in customary equipment such as hammer mills, blowing millsand air-jet mills and simultaneously or subsequently mixed with theformulation auxiliaries.

[0263] Emulsifiable concentrates are prepared by dissolving the activesubstance in an organic solvent, e.g. butanol, cyclohexanone,dimethylformamide, xylene or alternatively relatively high-boilingaromatics or hydrocarbons or mixtures of the organic solvents withaddition of one or more surfactants of ionic and/or nonionic type(emulsifiers). Examples of emulsifiers which can be used are:alkylarylsulfonic acid calcium salts such as Ca dodecylbenzenesulfonateor nonionic emulsifiers such as fatty acid polyglycol esters, alkylarylpolyglycol ethers, fatty alcohol polyglycol ethers, propyleneoxide-ethylene oxide condensation products, alkyl polyethers, sorbitanesters such as, for example, sorbitan fatty acid esters orpolyoxyethylene sorbitan esters such as, for example, polyoxyethylenesorbitan fatty acid esters.

[0264] Dusting agents are obtained by grinding the active substance withfinely divided solid substances, e.g. talc, natural clays, such askaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0265] Suspension concentrates can be water- or oil-based. They can beprepared, for example, by wet grinding by means of commerciallyavailable bead mills and, if appropriate, addition of surfactants, suchas have already been mentioned, for example, above in the case of theother formulation types.

[0266] Emulsions, e.g. oil-in-water emulsions (EW), can be prepared, forexample, by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and, if appropriate, surfactants, such as havealready been mentioned, for example, above in the case of the otherformulation types.

[0267] Granules can either be prepared by spraying the active substanceonto adsorptive, granulated inert material or by applying activesubstance concentrates to the surface of carriers such as sand,kaolinites or of granulated inert material by means of binders, e.g.polyvinyl alcohol, sodium polyacrylate or alternatively mineral oils.Suitable active substances can also be granulated in the mannercustomary for the preparation of fertilizer granules—if desired as amixture with fertilizers.

[0268] As a rule, water-dispersible granules are prepared by thecustomary processes such as spray-drying, fluidized bed granulation,disk granulation, mixing using high-speed mixers and extrusion withoutsolid inert material. For the preparation of disk, fluidized bed,extruder and spray granules, see, for example, processes in“Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J. E.Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff;“Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York1973, pp. 8-57.

[0269] For further details on the formulation of plant protectionmaterials see, for example, G. C. Klingman, “Weed Control as a Science”,John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer,S. A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell ScientificPublications, Oxford, 1968, pages 101-103.

[0270] As a rule, the agrochemical preparations contain 0.1 to 99% byweight, in particular 0.1 to 95% by weight, of active substance of theformula (I).

[0271] In wettable powders, the active substance concentration is, forexample, approximately 10 to 90% by weight, the remainder to 100% byweight consists of customary formulation constituents. In the case ofemulsifiable concentrates, the active substance concentration can beapproximately 1 to 90, preferably 5 to 80, % by weight. Formulations inthe form of dusts contain 1 to 30% by weight of active substance,preferably usually 5 to 20% by weight of active substance, sprayablesolutions contain approximately 0.05 to 80, preferably 2 to 50, % byweight of active substance. In the case of water-dispersible granules,the active substance content depends partly on whether the activecompound is liquid or solid and which granulation auxiliaries, fillersetc. are used. In the case of water-dispersible granules, the content ofactive substance is, for example, between 1 and 95% by weight,preferably between 10 and 80% by weight.

[0272] In addition, the active substance formulations mentionedoptionally contain the binders, wetting agents, dispersants,emulsifiers, penetrants, preservatives, antifreeze agents, solvents,fillers, carriers, colorants, antifoams, evaporation inhibitors and thepH and viscosity regulators which are customary in each case.

[0273] The compounds of the formula (I) or their salts can be employedas such or in the form of their preparations (formulations) ascombinations with other pesticidally active substances, such as, forexample, insecticides, acaricides, nematicides, herbicides, fungicides,safeners, fertilizers and/or growth regulators, for example as a premixor as tank mixes.

[0274] Components which may be employed for the active substancesaccording to the invention in mixed formulations or in tank mix are, forexample, known active compounds which are based on an inhibition of, forexample, acetolactate synthase, acetyl-coenzyme A carboxylase, PS I, PSII, HPPDO, phytoene desaturase, protoporphyrinogen oxidase, glutaminesynthetase, cellulose biosynthesis, 5-enolpyruvylshikimate-3-phosphatesynthetase. Such compounds, and also other compounds which can beemployed, whose mechanism of action is to a degree unknown or different,are described, for example, in Weed Research 26, 441-445 (1986), or “ThePesticide Manual”, 11th Edition 1997 (hereinbelow also abbreviated to“PM”) and 12th Edition 2000, The British Crop Protection Council and theRoyal Soc. of Chemistry (editors) and literature cited therein.Herbicides which are known from the literature and which can bementioned, which can be combined with the compounds of the formula (I),are, for example, the following active substances (Note: the compoundsare either designated by the common name according to the InternationalOrganization for Standardization (ISO) or using the chemical name, ifappropriate together with a customary code number): acetochlor;acifluorfen(-sodium); aclonifen; AKH 7088, i.e.[[[1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]aceticacid and its methyl ester; alachlor; alloxydim(-sodium); ametryn;amicarbazone, amidochlor, amidosulfuron; amatory; AMS, i.e. ammoniumsulfamate; anilofos; asulam; atrazin; azafenidin, azimsulfurone(DPX-A8947); aziprotryn; barban; BAS 516H, i.e.5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; beflubutamid,benazolin(-ethyl); benfluralin; benfuresate; bensulfuron(-methyl);bensulide; bentazone; benzobicyclon, benzofenap; benzofluor;benzoylprop(-ethyl); benzthiazuron; bialaphos; bifenox;bispyribac(-sodium), bromacil; bromobutide; bromofenoxim; bromoxynil;bromuron; buminafos; busoxinone; butachlor; butafenacil, butamifos;butenachlor; buthidazole; butralin; butroxydim, butylate; cafenstrole(CH-900); carbetamide; carfentrazone(-ethyl) (ICI-A0051); caloxydim,CDAA, i.e. 2-chloro-N,N-di-2-propenylacetamide; CDEC, i.e. 2-chloroallyldiethyldithiocarbamate; chlomethoxyfen; chloramben; chlorazifop-butyl,chlormesulon (ICI-A0051); chlorbromuron; chlorbufam; chlorfenac;chlorflurecolmethyl; chloridazon; chlorimuron(-ethyl); chlomitrofen;chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron;chlorthal-dimethyl; chlorthiamid; chlortoluron, cinidon(-methyl and-ethyl), cinmethylin; cinosulfuron; clefoxydim, clethodim; clodinafopand its ester derivatives (for example clodinafop-propargyl); clomazone;clomeprop; cloproxydim; clopyralid; clopyrasulfuron(-methyl),cloransulam(-methyl), cumyluron (JC 940); cyanazine; cycloate;cyclosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop and its esterderivatives (for example the butyl ester, DEH-112); cyperquat;cyprazine; cyprazole; daimuron; 2,4-D, 2,4-DB; 2,4-DB, dalapon;desmedipham; desmetryn; di-allate; dicamba; dichlobenil; dichlorprop;diclofop and its esters such as diclofop-methyl; diclosulam,diethatyl(-ethyl); difenoxuron; difenzoquat; diflufenican;diflufenzopyr, dimefuron; dimepiperate, dimethachlor; dimethametryn;dimethenamid (SAN-582H); dimethazone, dimexyflam, dimethipin;dimetrasulfuron, dinitramine; dinoseb; dinoterb; diphenamid;dipropetryn; diquat; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77,i.e. 5-cyano-1-(1,1-dimethylethyl)-N-methyl-1H-pyrazole-4-carboxamide;endothal; epoprodan, EPTC; esprocarb; ethalfluralin;ethametsulfuron-methyl; ethidimuron; ethiozin; ethofumesate; ethoxyfenand its esters (for example the ethyl ester, HN-252); ethoxysulfuron,etobenzanid (HW 52); F5231, i.e.N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide; fenoprop; fenoxan, fenoxaprop and fenoxaprop-P and their esters,for example fenoxaprop-P-ethyl and fenoxaprop-ethyl; fenoxydim;fentrazamide, fenuron; flamprop(-methyl or -isopropyl or -isopropyl-L);flazasulfuron; floazulate, florasulam, fluazifop and fluazifop-P andtheir esters, for example fluazifop-butyl and fluazifop-P-butyl;flucarbazone(-sodium), fluchloralin; flumetsulam; flumeturon;flumiclorac(-pentyl), flumioxazin (S-482); flumipropyn; fluometuron,fluorochloridone, fluorodifen; fluoroglycofen(-ethyl); flupoxam(KNW-739); flupropacil (UBIC-4243); flupyrsulfuron(-methyl or -sodium),flurenol(-butyl), fluridone; flurochloridone; fluroxypyr(-meptyl);flurprimidol, flurtamone; fluthiacet(-methyl), fluthiamide, fomesafen;foramsulfuron, fosamine; furyloxyfen; glufosinate(-ammonium);glyphosate(-isopropylammonium); halosafen; halosulfuron(-methyl) and itsesters (for example the methyl ester, NC-319); haloxyfop and its esters;haloxyfop-P (=R-haloxyfop) and its esters; hexazinone;imazamethabenz(-methyl); imazapyr; imazaquin and salts such as theammonium salt; imazamethapyr, imazamox, imazapic, imazethamethapyr;imazethapyr; imazosulfuron; indanofan, ioxynil; isocarbamid;isopropalin; isoproturon; isouron; isoxaben; isoxachlortole,isoxaflutole, isoxapyrifop; karbutilate; lactofen; lenacil; linuron;MCPA; MCPB; mecoprop; mefenacet; mefluidid; mesosulfuron, mesotrione,metamitron; metazachlor; methabenzthiazuron; metham; methazole;methoxyphenone; methyldymron; metabenzuron, methobenzuron; metobromuron;(alpha-)metolachlor; metosulam (XRD 511); metoxuron; metribuzin;metsulfuron-methyl; MH; molinate; monalide; monocarbamidedihydrogensulfate; monolinuron; monuron; MT 128, i.e.6-chloro-N-(3-chloro-2-propenyl)-5-methyl-N-phenyl-3-pyridazinamine; MT5950, i.e. N-[3-chloro-4-(1-methylethyl)-phenyl]-2-methylpentanamide;naproanilide; napropamide; naptalam; NC 310, i.e.4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole; neburon;nicosulfuron; nipyraclophen; nitralin; nitrofen; nitrofluorfen;norflurazon; orbencarb; oryzalin; oxadiargyl (RP-020630); oxadiazon;oxasulfuron, oxaziclomefone, oxyfluorfen; paraquat; pebulate; pelargonicacid, pendimethalin; pentoxazone, perfluidone; phenisopham;phenmedipham; picloram; picolinafen, piperophos; piributicarb;pirifenop-butyl; pretilachlor; primisulfuron(-methyl);procarbazone-(sodium), procyazine; prodiamine; profluralin;proglinazine(-ethyl); prometon; prometryn; propachlor; propanil;propaquizafop and its esters; propazine; propham; propisochlor;propyzamide; prosulfalin; prosulfocarb; prosulfuron (CGA-152005);prynachlor; pyraflufen(-ethyl), pyrazolinate; pyrazon;pyrazosulfuron(-ethyl); pyrazoxyfen; pyribenzoxim, pyributicarb,pyridafol, pyridate; pyrimidobac(-methyl), pyrithiobac(-sodium)(KIH-2031); pyroxofop and its esters (for example the propargyl ester);quinclorac; quinmerac; quinoclamine, quinofop and its ester derivatives,quizalofop and quizalofop-P and their ester derivatives, for examplequizalofop-ethyl; quizalofop-P-tefuryl and -ethyl; renriduron;rimsulfuron (DPX-E 9636); S 275, i.e.2-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4,5,6,7-tetrahydro-2H-indazole;secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, i.e.2-[[7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthalenyl]oxy]propanoicacid and its methyl ester; sulcotrione, sulfentrazon (FMC-97285,F-6285); sulfazuron; sulfometuron(-methyl); sulfosate (ICI-A0224);sulfosulfuron, TCA; tebutam (GCP-5544); tebuthiuron; tepraloxydim,terbacil; terbucarb; terbuchlor; terbumeton; terbuthylazine; terbutryn;TFH 450, i.e.N,N-diethyl-3-[(2-ethyl-6-methylphenyl)sulfonyl]-1H-1,2,4-triazole-1-carboxamide;thenylchlor (NSK-850); thiafluamide, thiazafluron; thiazopyr(Mon-13200); thidiazimin (SN-24085); thifensulfuron(-methyl);thiobencarb; tiocarbazil; tralkoxydim; tri-allate; triasulfuron;triaziflam, triazofenamide; tribenuron(-methyl); triclopyr; tridiphane;trietazine; trifluralin; triflusulfuron and its esters (for example themethyl ester, DPX-66037); trimeturon; tritosulfuron, tsitodef;vernolate; WL 110547, i.e.5-phenoxy-1-[3-(trifluoromethyl)phenyl]-1H-tetrazole; BAY MKH 6561,UBH-509; D-489; LS 82-556; KPP-300; NC-324; NC-330; KH-218; DPX-N8189;SC-0774; DOWCO-535; DK-8910; V-53482; PP-600; MBH-001; KIH-9201; ET-751;KIH-6127 and KIH-2023.

[0275] Controlling harmful plants selectively is of particular interestin crops of useful plants and ornamentals. Even though the compounds (I)already exhibit very good to sufficient selectivity in many crops, it ispossible, in principle, that symptoms of phytotoxicity occur on thecultivated plants in some crops and especially also in the case ofmixtures with other herbicides which are less selective. In thisrespect, combinations of compounds (I) according to the invention whichare of particular interest are those which contain the compounds (I) ortheir combinations with other herbicides or pesticides and safeners. Thesafeners, which are employed in such an amount that they act asantidote, reduce the phytotoxic side effects of theherbicides/pesticides employed, for example in economically importantcrops such as cereals (wheat, barley, rye, maize, rice, sorghum andmillet), sugar beet, sugar cane, oilseed rape, cotton and soybeans,preferably cereals. The following groups of compounds are examples ofsuitable safeners for the compounds (I) and their combinations withfurther pesticides:

[0276] a) compounds of the dichlorophenylpyrazoline-3-carboxylic acidtype, preferably compounds such as ethyl1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)5-methyl-2-pyrazoline-3-carboxylate (S1-1) (“Mefenpyr-diethyl”, PM, pp.781-782) and related compounds as they are described in WO 91/07874;

[0277] b) dichlorophenylpyrazolecarboxylic acid derivatives, preferablycompounds such as ethyl1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate(S1-4), ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate(S1-5) and related compounds as they are described in EP-A-333 131 andEP-A-269 806;

[0278] c) compounds of the triazolecarboxylic acids type, preferablycompounds such as fenchlorazol (and its ethyl ester), i.e. ethyl1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate(S1-6), and related compounds (see EP-A-174 562 and EP-A-346 620);

[0279] d) compounds of the 5-benzyl- or5-phenyl-2-isoxazoline-3-carboxylic acid type or the5,5-diphenyl-2-isoxazoline-3-carboxylic acid, preferably compounds suchas ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-7) orethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-8) and related compoundsas they are described in WO 91/08202, or ethyl5,5-diphenyl-2-isoxazolinecarboxylate (S1-9) (“isoxadifen-ethyl”) orn-propyl 5,5-diphenyl-2-isoxazolinecarboxylate (S1-10) or ethyl5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-11), as theyare described in German Patent Application (WO-A-95/07897);

[0280] e) compounds of the 8-quinolinoxyacetic acid type (S2),preferably 1-methylhex-1-yl (5-chloro-8-quinolinoxy)acetate (common name“cloquintocet-mexyl”) (S2-1) (see PM, pp. 263-264) 1,3-dimethylbut-1-yl(5-chloro-8-quinolinoxy)acetate (S2-2), 4-allyloxybutyl(5-chloro-8-quinolinoxy)acetate (S2-3), 1-allyloxyprop-2-yl(5-chloro-8-quinolinoxy)acetate (S2-4), ethyl(5-chloro-8-quinolinoxy)acetate (S2-5), methyl(5-chloro-8-quinolinoxy)acetate (S2-6), allyl(5-chloro-8-quinolinoxy)acetate (S2-7),2-(2-propylideneiminooxy)-1-ethyl (5-chloro-8-quinolinoxy)acetate(S2-8), 2-oxoprop-1-yl (5-chloro-8-quinolinoxy)acetate (S2-9), andrelated compounds as are described in EP-A-86 750, EP-A-94 349 andEP-A-191 736 or EP-A-0 492 366;

[0281] f) compounds of the (5-chloro-8-quinolinoxy)malonic acid type,preferably compounds such as diethyl (5-chloro-8-quinolinoxy)malonate,diallyl (5-chloro-8-quinolinoxy)malonate, methylethyl(5-chloro-8-quinolinoxy)malonate and related compounds as are describedin EP-A-0 582 198;

[0282] g) active substances of the phenoxyacetic or phenoxypropionicacid derivatives type or of the aromatic carboxylic acids type, such as,for example, 2,4-dichlorophenoxyacetic acids (and its esters) (2,4-D),4-chloro-2-methylphenoxypropionic esters (mecoprop), MCPA or3,6-dichloro-2-methoxybenzoic acid (and its esters) (dicamba);

[0283] h) active substances of the pyrimidines type which are employedin rice as soil-acting safeners, such as, for example, “fenclorim” (PM,pp. 511-512) (=4,6-dichloro-2-phenylpyrimidine), which is also known assafener for pretilachlor in seeded rice;

[0284] i) active substances of the dichloroacetamides type, which arefrequently employed as pre-emergence safeners (soil-acting safeners),such as, for example,

[0285] “dichlormid” (PM, pp. 363-364)(=N,N-diallyl-2,2-dichloroacetamide),

[0286] “R-29148” (=3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine, byStauffer),

[0287] “benoxacor” (PM, pp. 102-103)(=4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine),

[0288] “PPG-1292”(=N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide by PPGIndustries),

[0289] “DK-24” (=N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamideby Sagro-C hem),

[0290] “AD-67” or “MON 4660”(=3-dichloroacetyl-1-oxa-3-azaspiro[4,5]decane by Nitrokemia andMonsanto, respectively),

[0291] “diclonon” or “BAS145138” or “LAB145138”(=3-dichloroacetyl-2,5,5-trimethyl-1,3-diazabicyclo[4.3.0]nonane byBASF) and

[0292] “furilazol” or “MON 13900” (see PM, 637-638)(=(RS)-3-dichloroacetyl-5-(2-furyl-2,2-dimethyloxazolidine);

[0293] j) active substances of the dichloroacetone derivatives type,such as, for example,

[0294] “MG 191” (CAS Reg. No. 96420-72-3)(=2-dichloromethyl-2-methyl-1,3-dioxolane by Nitrokemia), which is knownas safener for maize;

[0295] k) active substances of the oxyimino compounds type, which areknown as seed treatment products, such as, for example,

[0296] “oxabetrinil” (PM, pp. 902-903)(=(Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)-acetonitrile), which isknown as seed-treatment safener for sorghum and millet againstmetolachlor damage,

[0297] “fluxofenim” (PM, pp. 613-614)(=1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanoneO-(1,3-dioxolan-2-ylmethyl)oxime, which is known as seed-dressingsafener for sorghum and millet against metolachlor damage, and

[0298] “cyometrinil” or “-CGA-43089” (PM, p. 1304)(=(Z)-cyanomethoxyimino(phenyl)acetonitrile), which is known asseed-treatment safener for sorghum and millet against metolachlordamage;

[0299] l) active substances of the thiazolecarboxylic ester type, whichare known as seed treatment products, such as, for example,

[0300] “flurazol” (PM, pp. 590-591) (=benzyl2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate), which is knownas seed-treatment safener for sorghum and millet against alachlor andmetolachlor damage;

[0301] m) active substances of the naphthalenedicarboxylic acidderivatives type, which are known as seed treatment products, such as,for example,

[0302] “naphthalic anhydride” (PM, p. 1342)(=1,8-naphthalenedicarboxylic anhydride), which is known asseed-treatment safener for maize against thiocarbamate herbicide damage;

[0303] n) active substances of the chromanacetic acid derivatives type,such as, for example,

[0304] “CL 304415” (CAS Reg. No. 31541-57-8)(=2-(4-carboxychroman-4-yl)acetic acid by American Cyanamid), which isknown as safener for maize against damage by imidazolinones;

[0305] o) active substances which, in addition to a herbicidal actionagainst harmful plants, also exhibit a safener action in connection withcrop plants such as rice, such as, for example,

[0306] “dimepiperate” or “MY-93” (PM, pp. 404405)(═S-1-methyl-1-phenylethyl piperidine-1-carbothioate), which is known assafener for rice against damage by the herbicide molinate,

[0307] “daimuron” or “SK 23” (PM, p. 330)(=1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as safenerfor rice against damage by the herbicide imazosulfuron,

[0308] “cumyluron”=“JC-940”(=3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, seeJP-A-60087254), which is known as safener for rice against damage byseveral herbicides,

[0309] “methoxyphenone” or “NK 049”(=3,3′-dimethyl-4-methoxybenzophenone), which is known as safener forrice against damage by several herbicides,

[0310] “CSB” (=1-bromo-4-(chloromethylsulfonyl)benzene) (CAS Reg. No.54091-064, by Kumiai), which is known as safener in rice against damageby several herbicides;

[0311] p) N-acylsulfonamides of the formula (S3) and their salts

[0312] as are described in WO-A-97/45016;

[0313] q) acylsulfamoylbenzamides of the formula (S4), if appropriatealso in salt form,

[0314] as are described in International Application No. PCT/EP98/06097;and

[0315] r) compounds of the formula (S5),

[0316] as are described in WO-A 98/13 361,

[0317] including the stereoisomers and the salts conventionally used inagriculture.

[0318] Amongst the safeners mentioned, those which are of particularinterest are (S1-1) and (S1-9) and (S2-1), in particular (S1-1) and(S1-9).

[0319] Some of the safeners are already known as herbicides andtherefore simultaneously also display a protective action in connectionwith the crop plants in addition to the herbicidal action in connectionwith harmful plants.

[0320] The weight ratio of herbicide (mixture) to safener generallydepends on the application rate of herbicide and the efficacy of thesafener in question; it can vary within wide limits, for example in therange of from 200:1 to 1:200, preferably from 100:1 to 1:100, inparticular 20:1 to 1:20. The safeners can be formulated with furtherherbicides/pesticides, analogously to the compounds (I) or theirmixtures, and provided and used as readymix or tank mix together withthe herbicides.

[0321] For use, the herbicide or herbicide safener formulations, whichare present in a customary commercial form, are, if appropriate, dilutedin the customary fashion, for example using water in the case ofwettable powders, emulsifiable concentrates, dispersions andwater-dispersible granules. Preparations in the form of dusts, soilgranules, granules for spreading, and sprayable solutions, are usuallynot diluted further with other inert materials prior to use.

[0322] The application rate required of the compounds of the formula (I)varies with, inter alia, the external conditions such as temperature,humidity and the type of the herbicide used. It can vary within widelimits, for example between 0.001 and 10.0 kg/ha or more of activesubstance, but it is preferably between 0.005 and 5 kg/ha, in particular0.01 and 3 kg/ha.

[0323] In the examples which follow, quantities (also percentages) areweight-based, unless specifically indicated.

A. CHEMICAL EXAMPLES Example A12-Dimethylaminomethyleneamino-4-(1-fluoro-1-methylethyl)-6-(1-cyclopropyl-4-phenyl-1-butylamino)-1,3,5-triazine(see Table 8, Example 8-2)

[0324] A solution of 1.71 g (5 mmol) of2-amino-4-(1-fluoro-1-methylethyl)-6-(1-cyclopropyl-4-phenyl-1-butylamino)-1,3,5-triazineand 2 ml of N,N-dimethylformamide dimethyl acetal in 30 ml of toluene isrefluxed for 2 hours. All volatile constituents are subsequentlycarefully distilled off. This gives 1.94 g (97.5% of theory) of2-dimethylaminomethyleneamino-4-(1-fluoro-1-methylethyl)₆-(1-cyclopropyl-4-phenyl-1-butylamino)-1,3,5-triazineas colorless oil.

Example A2N-[4-(1-Fluoro1-methylethyl)-6-(1-cyclopropyl-4-phenyl-1-butylamino)-1,3,5-triazin-2-yl]formamideoxime (see Table 8, Example 8-27)

[0325] 0.69 g (10 mmol) of hydroxylamine hydrochloride are added withstirring at room temperature to a solution of 1.99 g (5 mmol) of2-dimethylaminomethyleneamino-4-(1-fluoro-1-methylethyl)₆-(1-cyclopropyl-4phenyl-1-butylamino)1,3,5-triazinein 20 ml of methanol. The reaction mixture is stirred for 2 hours atroom temperature. All volatile constituents are carefully distilled off.The crude product is taken up in methylene chloride. The mixture iswashed with water, dried over Na₂SO₄ and evaporated in vacuo. This gives1.81 g (93.7% of theory) of N-[4-(1-fluoro-1-methylethyl)-6-(1-cyclopropyl-4-phenyl-1-butylamino)-1,3,5-triazin-1-yl]formamideoxime as pale yellow oil.

Example A32-(4-Chlorobenzylideneamino)-4-(1-fluoro-1-methylethyl)-6-(1-cyclopropyl-4-phenyl-1-butylamino)-1,3,5-triazine(see Table 8, Example 8-37)

[0326] A mixture of 2.5 g (7.28 mmol) of2-amino-4-(1-fluoro-1-methylethyl)-6-(1-cyclopropyl-4-phenyl-1-butylamino)-1,3,5-triazine,1.08 g (7.70 mmol) of p-chlorobenzaldehyde and 100 mg ofp-toluenesulfonic acid in 80 ml of toluene are boiled for 10 hours in awater separator. When cold, all volatile constituents are distilled. Thecrude product is purified by column chromatography (eluent:toluene/ethylacetate=85:15). This gives 3.0 g (89% of theory) of2-(4-chloro-6-benzylideneamino)₄-(1-fluoro-1-methylethyl-)-6-(1-cyclopropyl-4-phenyl-1-butylamino)-1,3,5-triazineas colorless oil.

[0327] The compounds described in Tables 1 to 12 hereinbelow areobtained in accordance with, or analogously to, the above Examples A1 toA3 or the methods which have been described in general further above. Inthe tables, the abbreviations have the following meanings: Me = methylEt = ethyl Pr = propyl i-Pr = isopropyl c-Pr = cyclopropyl c-Bu =cyclobutyl t-Bu = tertiary butyl c-hexyl = cyclohexyl A1 = (CH₂)₁ =—CH₂— Ph = phenyl Bz = benzyl A2 = (CH₂)₂ = —CH₂CH₂— A3 = (CH₂)₃ =—CH₂CH₂CH₂— A4 = (CH₂)₄ = —CH₂CH₂CH₂CH₂— Ac = COCH₃ = acetyl Ox =

= oxiranyl Ph = phenyl (X)_(n) = “—” corresponds to n = 0

[0328] Tables 1 to 11 which follow refer to formula (I) where L⁰=adirect bond and R⁴=hydrogen atom: TABLE 1 (I)

Physical data and stereochemical No. R¹ A²-R² R³ A¹ (X)_(n) information1-1 CH₂OCH₃ c-Pr N═CH—NMe₂ A¹ 4-Cl racemate 1-2 CH(CH₃)(OCH₃) c-PrN═CH—NMe₂ A¹ 4-Cl racemate 1-3 CHMe₂ c-Pr N═CH—NMe₂ A¹ 4-F racemate 1-4CH₂OEt c-Pr N═C(Et)NEt₂ A¹ 4-Cl racemate 1-5 CH₂CF₃ c-Pr N═C(Ph)(NMe₂)A¹ 4-Cl racemate 1-6 Ph c-Bu N═C(4-MePh)(NMe₂) A¹ 4-Br racemate 1-7CH₂Ph c-Bu- N═C(CH₂Ph)(NMe₂) A¹ 4-Cl racemate 1-8 CH(CH₃)(CH₂CF₃)c-phenyl N═C(OMe)(NMe₂) A¹ 4-Br racemate 1-9 Me c-Pr NH—CH═N—OH A¹ 4-Clracemate 1-10 Et c-Pr NH—CH═N—OH A¹ 2,4-Cl₂ racemate 1-11 c-Pr c-PrNH—CH═N—NH₂ A¹ 2,4-Cl₂ racemate 1-12 c-Pr c-Pr NH—CH═N—NMe₂ A¹ 2,4,6-Cl₃racemate 1-13 c-Bu CH₂Ph NHN═CHN(Ph)₂ A¹ 4-Cl racemate 1-14 c-Bu CH₂PhN═CHPh A¹ — racemate

[0329] Physical data and stereochemical No. R¹ A²R² R³ A¹ (X)_(n)information 2-1 CHMe₂ c-Pr N═CH—NMe₂ A² — racemate, oil 2-2 CHFMe c-PrN═CH—NMe₂ A² 4-J racemate 2-3 CHFEt c-Pr N═CH—NMe₂ A² 3-Br racemate 2-4CFMe₂ c-Pr N═CH—NMe₂ A² 4-Na racemate 2-5 Me c-Pr N═CH—NMe₂ A² —racemate 2-6 Et c-Pr N═CH—NMe₂ A² — racemate 2-7 CHMe₂ c-PrN═C(Me)(NMe₂) A² — racemate 2-8 CFMe₂ c-Pr N═C(Me)(NMe₂) A² 4-CF₃racemate 2-9 CHFMe c-Pr N═C(Me)(NMe₂) A² 4-CF₃ racemate 2-10 CHFEt c-PrN═C(Me)(NMe₂) A² 4-CF₃ racemate 2-11 CFMe₂ c-Pr N═CH—NEt₂ A² 4-CF₃racemate 2-12 CHFEt c-Pr N═CH—NEt₂ A² 4-CF₃ racemate 2-13 CHMe₂ c-PrN═CH—NEt₂ A² 4-CF₃ racemate 2-14 CFMe₂ c-Pr N═C(Me)N(CH₂CH₂OH)₂ A² 4-CF₃racemate 2-15 CFMe₂ c-Pr N═CH—NEt₂ A² — racemate 2-16 CFMe₂ c-PrN═CH—NEt₂ A² 3-Me racemate 2-17 CFMe₂ c-Pr N═CH—NEt₂ A² 3-Cl racemate2-18 CFMe₂ c-Pr N═CH—NEt₂ A² 3,5-Me₂ racemate 2-19 CFMe₂ c-Pr N═CH—NEt₂A² 3-F racemate 2-20 CHFMe c-Pr N═CH—NEt₂ A² — racemate 2-21 CHFMe c-PrN═CH—NEt₂ A² 3-Me racemate 2-22 CHFMe c-Pr N═CH—NEt₂ A² 3-Cl racemate2-23 CHFMe c-Pr N═CH—NEt₂ A² 3,5-Me₂ racemate 2-24 CHFMe c-Pr N═CH—NEt₂A² 3-F racemate 2-25 CHFEt c-Pr N═CH—NEt₂ A² — racemate 2-26 CHEEt c-PrN═CH—NEt₂ A² 3-Me racemate 2-27 CHFEt c-Pr N═CH—NEt₂ A² 3-Cl racemate2-28 CHFEt c-Pr N═CH—NEt₂ A² 3,5-Me₂ racemate 2-29 CHFEt c-Pr N═CH—NEt₂A² 3-F racemate 2-30 CFMe₂ c-Pr N═CH—NMe₂ A² — racemate 2-31 CFMe₂ c-PrN═CH—NMe₂ A² 3-Me racemate 2-32 CFMe₂ c-Pr N═CH—NMe₂ A² 3-Cl racemate2-33 CFMe₂ c-Pr N═CH—NMe₂ A² 3,5-Me₂ racemate 2-34 CFMe₂ c-Pr N═CH—NMe₂A² 3-F racemate 2-35 CHFMe c-Pr N═CH—NMe₂ A² — racemate, oil 2-36 CHFMec-Pr N═CH—NMe₂ A² 3-Me racemate, oil 2-37 CHFMe c-Pr N═CH—NMe₂ A² 3-Clracemate 2-38 CHFMe c-Pr N═CH—NMe₂ A² 3,5-Me₂ racemate 2-39 CHEMe c-PrN═CH—NMe₂ A² 3-F racemate 2-40 CHFEt c-Pr N═CH—NMe₂ A² — racemate 2-41CHFEt c-Pr N═CH—NMe₂ A² 3-Me racemate 2-42 CHFEt c-Pr N═CH—NMe₂ A² 3-Clracemate 2-43 CHFEt c-Pr N═CH—NMe₂ A² 3,5-Me₂ racemate 2-44 CHFEt c-PrN═CH—NMe₂ A² 3-F racemate 2-45 CFMe₂ c-Pr N═C(Me)NMe₂ A² — racemate, oil2-46 CFMe₂ c-Pr N═C(Me)NMe₂ A² 3-Me racemate 2-47 CFMe₂ c-Pr N═C(Me)NMe₂A² 3-Cl racemate 2-48 CFMe₂ c-Pr N═C(Me)NMe₂ A² 3,5-Me₂ racemate 2-49CFMe₂ c-Pr N═C(Me)NMe₂ A² 3-F racemate 2-50 CHFMe c-Pr N═C(Me)NMe₂ A² —racemate 2-51 CHFMe c-Pr N═C(Me)NMe₂ A² 3-Me racemate 2-52 CHFMe c-PrN═C(Me)NMe₂ A² 3-Cl racemate 2-53 CHFMe c-Pr N═C(Me)NMe₂ A² 3,5-Me₂racemate 2-54 CHFMe c-Pr N═C(Me)NMe₂ A² 3-F racemate 2-55 CHFEt c-PrN═C(Me)NMe₂ A² — racemate, oil 2-56 CHFEt c-Pr N═C(Me)NMe₂ A² 3-Meracemate, oil 2-57 CHEEt c-Pr N═C(Me)NMe₂ A² 3-Cl racemate 2-58 CHFEtc-Pr N═C(Me)NMe₂ A² 3,5-Me₂ racemate 2-59 CHFEt c-Pr N═C(Me)NMe₂ A² 3-Fracemate 2-60 CFMe₂ c-Pr N═CHNMe₂ OA1 — racemate 2-61 CHEEr c-PrN═CHNMe₂ OA1 — racemate 2-62 CClMe₂ c-Pr N═C(Me)(NMe₂) OA1 — racemate2-63 CHCeMe c-Pr N═CHNEt₂ OA1 — racemate 2-64 Me c-Pr N═C(Et)(NEt₂) OA1— racemate 2-65 Et c-Pr N═C(Pr)(NMe₂) OA1 — racemate 2-66 CHMe₂ c-PrN═C(Ph)(NEt₂) OA1 — racemate 2-67 CFMe₂ c-Pr N═C(n-Bu)(NMe₂) OA13,5-(OMe)₂ racemate 2-68 CFMe₂ c-Pr NH═N═CHNMe₂ OA1 — racemate 2-69CFMe₂ c-Pr N═C(Me)(NMe₂) OA1 3,5-Cl₂ racemate 2-70 CFMe₂ c-PrN═C(Me)C(NPh₂) OA1 3,5-F₂ racemate 2-71 CBrMe₂ c-Pr NC(Me)(NEt2) OA12,5-F₂ racemate 2-72 CClMe₂ c-Pr NCHN(n-Pr)₂ OA1 — racemate 2-73 CHFEtc-Pr NH—CH═N—OH A2 — racemate 2-74 CHFEt₂ c-Pr NH—CH═N—OH A2 3-Clracemate 2-75 CHFEt₂ c-Pr NH—CH═N—OH A2 3-F racemate 2-76 CHFEt₂ c-PrNH—CH═N—OH A2 4-F, 3-Me racemate 2-77 CHFEt₂ c-Pr NH—CH═N—OH A2 3,4-F₂racemate 2-78 CFMe₂ c-Pr N═CH—Ph A2 — racemate 2-79 CFMe₂ c-PrN═CH—4-Cl-C₆H₄ A2 — racemate 2-80 CFMe₂ c-Pr N═CH-4-F—C₆H₄ A2 — racemate2-81 CFMe₂ c-Pr N═CH-3,4-F₂—C₈H₃ A2 — racemate 2-82 CHFMe c-PrN═C(Me)(C₆H₅) A2 — racemate 2-83 CHFMe c-Pr NH—N═CHNMe₂ A2 3,5-Me₂racemate 2-84 CHFMe c-Pr NH—N═CHCHNMe₂ A2 3,4-Me₂ racemate 2-85 CHFMec-Pr NH—N═CHNMe₂ A2 3-OEt racemate 2-86 CHFMe c-Pr NH—N═CHNMe₂ A2 3-OCF₃racemate 2-87 CHFMe c-Pr NH—N═CHNMe₂ A2 3-OCHF₂ racemate 2-88 CFMe₂ c-Pr

A2 — racemate 2-89 CFMe₂ c-Pr

A2 — racemate 2-90 CFMe₂ c-Pr

A2 — racemate

[0330] TABLE 3 Physical data and stereochemical No. R¹ R³ A¹ (X)_(n)information 3-1 CFMe₂ c-Bu N═CH—NMe₂ A2 — racemate, oil 3-2 CFMe₂ c-BuN═CH—NMe₂ A2 3-Cl racemate 3-3 CHFMe c-Bu N═CH—NMe₂ A2 3-OEt racemate3-4 CHFMe c-Bu N═CH—NMe₂ A2 3,5-Me₂ racemate 3-5 CHMe₂ c-Bu N═CH—NMe₂ A23-O-i-Pr racemate 3-6 CHFMe c-Bu N═CH—NMe₂ A2 — racemate 3-7 CHFEt c-BuN═CH—NMe₂ A2 — racemate 3-8 Me c-Bu N═CH—NMe₂ A2 — racemate 3-9 Et c-BuN═CH—NMe₂ A2 — racemate 3-10 CF3 c-Bu N═CH—NMe₂ A2 — racemate 3-11CClMe₂ c-Bu N═NH—NMe₂ A2 — racemate 3-12 CH₂—O—CH₃ c-Bu N═CH—NM₂ A2 —racemate 3-13 CF₃ c-Bu N═C(Me)(NMe₂) A2 — racemate 3-14 CFMe₂ c-BuN═C(Me)(NMe₂) A2 — racemate, oil 3-15 CHFMe c-Bu N═C(Me)(NMe₂) A2 —racemate 3-16 CHFEt c-Bu N═C(Me)(NMe₂) A2 — racemate 3-17 Me c-BuN═C(Me)(NMe₂) A2 — racemate 3-18 c-Pr c-Bu N═C(Me)(NMe₂) A2 — racemate3-19 CFMe₂ c-Bu N═C(Me)(NMe2) A2 3-F racemate 3-20 CFMe₂ c-BuN═C(Me)(NMe2) A2 3-CF₃ racemate 3-21 CHFMe c-Bu N═C(Me)(NMe₂) A2 3-Clracemate 3-22 CFMe₂ c-Bu N═C(Me)(NMe₂) A2 3,4-Me₂ racemate 3-23 CClMe₂c-Bu N═C(Me)(NMe₂) A2 3-Cl, 5-Me racemate 3-24 c-Pr c-Bu N═C(Me)(NMe₂)A2 3,5-Me₂ racemate 3-25 c-Pr c-Bu N═C(Et)(NMe₂) A2 — racemate, oil 3-26CFMe₂ c-Bu N═CHNEt₂ A2 — racemate 3-27 CHMe₂ c-Bu N═CHNEt₂ A2 — racemate3-28 CF₃ c-Bu N═CHNEt₂ A2 — racemate 3-29 CH₂F c-Bu N═CHNEt₂ A2 —racemate 3-30 CFMe₂ c-Bu N═CHN(CH₂CH₂OH)₂ A2 — racemate 3-31 CCH₂Me c-BuN═C(Ph)(NEt₂) A2 — racemate 3-32 CCH₂Cl c-Bu N═C(Ph)(NEt₂) A2 — racemate3-33 CCl₃ c-Bu N═C(Ph)(NEt₂) A2 — racemate 3-34 CHCl₂ c-BuN═C(Ph)(N—Pr₂) A2 — racemate 3-35 CH₂Cl c-Bu N═C(3-Cl—Ph)(NMe₂) A23,4-Cl₂ racemate 3-36 CFMe₂ c-Bu N═C(Me)—NMe₂ A2 3-Me racemate 3-37CFMe₂ c-Bu N═C(Me)—NMe₂ A2 3,4-F₂ racemate, oil 3-38 CFMe₂ c-BuN═C(Me)—NMe₂ A2 3-OMe racemate, oil 3-39 CFMe₂ c-Bu N═C(Me)—NMe₂ A23,4-(OMe)₂ racemate 3-40 CFMe₂ c-Bu N═C(Me)—NMe₂ A2 3-F racemate, oil3-41 CFMe₂ c-Bu N═C(Me)—NMe₂ A2 4-F racemate, oil 3-42 CHFMe c-BuN═C(Me)—NMe₂ A2 3-Me racemate 3-43 CHEMe c-Bu N═C(Me)—NMe₂ A2 3,4-F₂racemate, oil 3-44 CHFMe c-Bu N═C(Me)—NMe₂ A2 3-OMe racemate, oil 3-45CHFMe c-Bu N═C(Me)—NMe₂ A2 3,4-(OMe)₂ racemate 3-46 CHFMe c-BuN═C(Me)—NMe₂ A2 3-F racemate, oil 3-47 CHFMe c-Bu N═C(Me)—NMe₂ A2 4-Fracemate, oil 3-48 CHFEt c-Bu N═C(Me)—NMe₂ A2 3-Me racemate 3-49 CHFEtc-Bu N═C(Me)—NMe₂ A2 3,4-F₂ racemate 3-50 CHFEt c-Bu N═C(Me)—NMe₂ A23-OMe racemate 3-51 CHFEt c-Bu N═C(Me)—NMe₂ A2 3,4-(OMe)₂ racemate 3-52CHFEt c-Bu N═C(Me)—NMe₂ A2 3-F racemate 3-53 CHFEt c-Bu N═C(Me)—NMe₂ A24-F racemate 3-54 CFMe₂ c-Bu N═CH—NMe₂ A2 3-Me racemate 3-55 CFMe₂ c-BuN═CH—NMe₂ A2 3,4-F₂ racemate, oil 3-56 CFMe₂ c-Bu N═CH—NMe₂ A2 3-OMeracemate, oil 3-57 CFMe₂ c-Bu N═CH—NMe₂ A2 3,4-(OMe)₂ racemate 3-58CFMe₂ c-Bu N═CH—NMe₂ A2 3-F racemate, oil 3-59 CFMe₂ c-Bu N═CH—NMe₂ A24-F racemate, oil 3-60 CHFMe c-Bu N═CH—NMe₂ A2 3-Me racemate 3-61 CHFMec-Bu N═CH—NMe₂ A2 3,4-F₂ racemate 3-62 CHEMe c-Bu N═CH—NMe₂ A2 3-OMeracemate 3-63 CHFMe c-Bu N═CH—NMe₂ A2 3,4-(OMe)₂ racemate 3-64 CHFMec-Bu N═CH—NMe₂ A2 3-F racemate 3-65 CHFMe c-Bu N═CH—NMe₂ A2 4-F racemate3-66 CHFMe c-Bu N═CH—NMe₂ A2 3-Me racemate 3-67 CHFEt c-Bu N═CH—NMe₂ A23,4-F₂ racemate, oil 3-68 CHFEt c-Bu N═CH—NMe₂ A2 3-OMe racemate, oil3-69 CHFEt c-Bu N═CH—NMe₂ A2 3,4-(OMe)₂ racemate 3-70 CHFEt c-BuN═CH—NMe₂ A2 3-F racemate, oil 3-71 CHEEt c-Bu N═CH—NMe₂ A2 4-Fracemate, oil 3-72 CFME₂ c-Bu N═CH—NEt₂ A2 3-Me racemate 3-73 CFMe₂ c-BuN═CH—NEt₂ A2 3,4-F₂ racemate 3-74 CFMe₂ c-Bu N═CH—NEt₂ A2 3-OMeracemate, oil 3-75 CFMe₂ c-Bu N═CH—NEt₂ A2 3,4-(OMe)₂ racemate 3-76CFMe₂ c-Bu N═CH—NEt₂ A2 3-F racemate 3-77 CFMe₂ c-Bu N═CH—NEt₂ A2 4-Fracemate 3-78 CHEMe c-Bu N═CH—NEt₂ A2 3-Me racemate 3-79 CHFMe c-BuN═CH—NEt₂ A2 3,4-F₂ racemate 3-80 CHFMe c-Bu N═CH—NEt₂ A2 3-OMe racemate3-81 CHFMe c-Bu N═CH—NEt₂ A2 3,4-(OMe)₂ racemate 3-82 CHFMe c-BuN═CH—NEt₂ A2 3-F racemate 3-83 CHFMe c-Bu N═CH—NEt₂ A2 4-F racemate 3-84CHFEt c-Bu N═CH—NEt₂ A2 3-Me racemate 3-85 CHFEt c-Bu N═CH—NEt₂ A23,4-F₂ racemate, oil 3-86 CHFEt c-Bu N═CH—NEt₂ A2 3-OMe racemate, oil3-87 CHFEt c-Bu N═CH—NEt₂ A2 3,4-(OMe)₂ racemate 3-88 CHEEt c-BuN═CH—NEt₂ A2 3-F racemate 3-89 CHFEt c-Bu N═CH—NEt₂ A2 4-F racemate 3-90CHFEt c-Bu NH—CH═N—OH OA1 — racemate 3-91 CHFMe c-Bu —NH—CH═N—OH OA1 —racemate 3-92 CFMe c-Bu —NH—CH═N—NH₂ OA1 — racemate 3-93 CHFEt c-Bu—NH—CH═N—NMe₂ OA1 — racemate 3-94 CFMe₂ c-Bu N═CHPh OA1 — racemate 3-95CFMe₂ c-Bu N═CH-3-Cl—C₆H₃ OA1 — racemate 3-96 CF₃ c-Bu N═CHPh OA13,5-Me₂ racemate 3-97 CF₃ c-Bu N═CHPh OA1 3-F, 4-Me racemate 3-98 CF₃c-Bu N═CHPh OA1 3,5-Cl₂ racemate 3-99 CF₃ c-Bu N═CHPh OA1 3-Cl racemate3-100 CF₃ c-Bu N═CHPh OA1 3,4-F₂ racemate 3-101 CHF₂ c-Bu N═CHPh OA12-Cl racemate 3-102 CH₂F c-Bu N═CH-2,3-Cl₂—C₆H₃ OA1 2,5-Cl₂ racemate3-103 CFMe₂ c-Bu N═CH-3,5-Cl₂C₆H₃ OA1 2,6-Cl₂ racemate 3-104 CFMe₂ c-BuN═CH—NMe₂ A2 — R enantiomer 3-105 CFMe₂ c-Bu N═CH—NMe₂ A2 — S enantiomer3-106 CFMe₂ c-Bu N═CH—NMe₂ OA1 — R enantiomer 3-107 CFMe₂ c-Bu N═CH—NMe₂OA1 — S enantiomer 3-108 CHMe₂ c-Bu NH—CH═N—OH A2 3-F racemate 3-109CHBrMe c-Bu NH—CH═N—OH A2 3-CF₃ racemate 3-110 CHFMe c-Bu NHN═CHNMe₂ A2— racemate 3-111 CFMe₂ c-Bu NHN═CHNEt₂ A2 — racemate 3-112 CFMe₂ c-BuNH—NH—CH═NMe A2 — racemate 3-113 CFMe₂ c-Bu NH—CH═N—OH A2 — racemate3-114 CFMe₂ c-Bu NH—CH═N—OH A2 4-Br racemate 3-115 CFMe₂ c-Bu NH—CH═N—OHA2 4-NO₂ racemate 3-116 CFMe₂ c-Bu N═CHPh A2 3-NO₂ racemate 3-117 CFMe₂c-Bu N═CH-4-Cl—C₆H₄ A2 2-NO₂ racemate 3-118 CFMe₂ c-Bu N═CH-3-CH₃—C₆H₄A2 3-Cl racemate 3-119 CFMe₂ c-Bu N═CH-3-CF₃—C₆H₄ A2 2,6-Cl₂ racemate3-120 CHFMe₂ c-Bu

A2 — racemate 3-121 CFMe₂ c-Bu

A2 — racemate 3-122 CFMe₂ c-Bu

A2 — racemate 3-123 CFMe₂ c-Bu

A2 — racemate 3-124 CFMe₂ c-Bu

A2 — racemate, oil 3-125 CFMe₂ c-Bu

A2 — racemate 3-126 H c-Bu N═CH—NEt₂ A2 — racemate 3-127 CFMe₂ c-BuNHN═CHNMe₂ A2 — racemate

[0331] TABLE 4 Physical data and stereochemical No. R¹ A²-R² R3 A1(X)_(n) information 4-1 CFMe₂ c-pentyl N═CHNMe₂ A2 — racemate 4-2 CFMe₂c-pentyl N═CHNMe₂ A2 3,4-F₂ racemate 4-3 CClMe₂ c-pentyl N═CHNMe₂ A2 —racemate 4-4 CHCl₂ c-pentyl N═CHNMe₂ A2 — racemate 4-5 i-Pr c-hexylN═CHNMe₂ A2 — racemate 4-6 i-Bu c-hexyl N═C(Me)NMe₂ A2 — racemate 4-7CFMe₂ c-pentyl

A2 — racemate

[0332] TABLE 5 Physical data and stereochemical No. R¹ A²-R² R³ A¹(X)_(n) information 5-1  CFMe₂ CH₂-c-Pr N═CH—NEt₂ A2 3-Me racemate, oil5-2  CFMe₂ CH₂-c-Pr N═CH—NEt₂ A2 3-OMe racemate 5-3  CFMe₂ CH₂-c-PrN═CH—NEt₂ A2 3-Cl racemate 5-4  CFMe₂ CH₂-c-Pr N═CH—NEt₂ A2 — racemate5-5  CHFMe CH₂-c-Pr N═CH—NEt₂ A2 3-Me racemate 5-6  CHFMe CH₂-c-PrN═CH—NEt₂ A2 3-OMe racemate 5-7  CHFMe CH₂-c-Pr N═CH—NEt₂ A2 3-Clracemate 5-8  CHFMe CH₂-c-Pr N═CH—NEt₂ A2 — racemate 5-9  CHFEt CH₂-c-PrN═CH—NEt₂ A2 3-Me racemate 5-10 CHFEt CH₂-c-Pr N═CH—NEt₂ A2 3-OMeracemate 5-11 CHFEt CH₂-c-Pr N═CH—NEt₂ A2 3-Cl racemate 5-12 CHFEtCH₂-c-Pr N═CH—NEt₂ A2 — racemate 5-13 CHMe₂ CH₂-c-Pr N═CH—NEt₂ A2 3-Meracemate 5-14 CHMe₂ CH₂-c-Pr N═CH—NEt₂ A2 3-OMe racemate 5-15 CHMe₂CH₂-c-Pr N═CH—NEt₂ A2 3-Cl racemate 5-16 CHMe₂ CH₂-c-Pr N═CH—NEt₂ A2 —racemate 5-17 CFMe₂ CH₂-c-Pr N═C(Me)—NMe₂ A2 3-Me racemate 5-18 CFMe₂CH₂-c-Pr N═C(Me)—NMe₂ A2 3-OMe racemate, oil 5-19 CFMe₂ CH₂-c-PrN═C(Me)—NMe₂ A2 3-Cl racemate 5-20 CFMe₂ CH₂-c-Pr N═C(Me)—NMe₂ A2 —racemate 5-21 CHFMe CH₂-c-Pr N═C(Me)—NMe₂ A2 3-Me racemate 5-22 CHFMeCH₂-c-Pr N═C(Me)—NMe₂ A2 3-OMe racemate 5-23 CHFMe CH₂-c-Pr N═C(Me)—NMe₂A2 3-Cl racemate 5-24 CHFMe CH₂-c-Pr N═C(Me)—NMe₂ A2 — racemate 5-25CHFEt CH₂-c-Pr N═C(Me)—NMe₂ A2 3-Me racemate 5-26 CHFEt CH₂-c-PrN═C(Me)—NMe₂ A2 3-OMe racemate 5-27 CHFEt CH₂-c-Pr N═C(Me)—NMe₂ A2 3-Clracemate 5-28 CHFEt CH₂-c-Pr N═C(Me)—NMe₂ A2 — racemate 5-29 CFMe₂CH₂-c-Pr N═C(Me)—NMe₂ A2 3-Me racemate 5-30 CFMe₂ CH₂-c-Pr N═C(Me)—NMe₂A2 3-OMe racemate 5-31 CFMe₂ CH₂-c-Pr N═C(Me)—NMe₂ A2 3-Cl racemate 5-32CFMe₂ CH₂-c-Pr N═C(Me)—NMe₂ A2 — racemate 5-33 CFMe₂ CH₂-c-Pr N═CH—NMe₂A2 3-Me racemate 5-34 CFMe₂ CH₂-c-Pr N═CH—NMe₂ A2 3-OME racemate 5-35CFMe₂ CH₂-c-Pr N═CH—NMe₂ A2 3-Cl racemate 5-36 CFMe₂ CH₂-c-Pr N═CH—NMe₂A2 — racemate, oil 5-37 CHFMe CH₂-c-Pr N═CH—NMe₂ A2 3-Me racemate 5-38CHFMe CH₂-c-Pr N═CH—NMe₂ A2 3-OME racemate 5-39 CHFMe CH₂--Pr N═CH—NMe₂A2 3-Cl racemate 5-40 CHFMe CH₂-c-Pr N═CH—NMe₂ A2 — racemate, oil 5-41CHFEt CH₂-c-Pr N═CH—NMe₂ A2 3-Me racemate 5-42 CHFEt CH₂--Pr N═CH—NMe₂A2 3-OMe racemate 5-43 CHFEt CH₂-c-Pr N═CH—NMe₂ A2 3-Cl racemate 5-44CHFEt CH₂-c-Pr N═CH—NMe₂ A2 — racemate 5-45 CHMe₂ CH₂-c-Pr N═CH—NMe₂ A23-Me racemate 5-46 CHMe₂ CH₂-c-Pr N═CH—NMe₂ A2 3-OMe racemate 5-47 CHMe₂CH₂-c-Pr N═CH—NMe₂ A2 3-Cl racemate 5-48 CHMe₂ CH₂-c-Pr N═CH—NMe₂ A2 —racemate 5-49 CFMe₂ CH₂-c-Pr N═CH—NMe₂ OA1 — racemate 5-50 CHMe₂CH₂-c-Pr N═CH—NMe₂ OA1 — racemate 5-51 Ph CH₂-c-Pr N═CH—NMe₂ OA1 —racemate 5-52 c-Bu CH₂-c-Pr N═CH—NMe₂ SA1 — racemate 5-53 c-pentylCH₂-c-Pr N═CH—NMe₂ SA1 — racemate 5-54 c-Pr CH₂-c-Pr N═CH—NMe₂ SA1 —racemate 5-55 CF₃ CH₂-c-Pr N═CH—NMe₂ SA1 — racemate 5-56 CFMe₂ CH₂-c-PrN═CH—NMe₂ NMeA1 — racemate 5-57 CHFMe CH₂-c-Pr N═CH—NMe₂ NMe-A1 —racemate 5-58 CFMe₂ CH₂-c-Pr N═CH—NMe₂ NEt-A1 — racemate 5-59 CHFPrCH₂-c-Pr N═CH—NMe₂ NEt-A1 — racemate 5-60 CH₂CH₂CF₃ CH₂-c-Pr N═CH—NMe₂NPh-A1 — racemate 5-61 CF₂CHF₂ CH₂-c-Pr N═CH—NMe₂ NPh-A1 — racemate 5-62CFCl₂ CH₂-c-Pr N═CH—NMe₂ NBz-A1 2-NO₂ racemate 5-63 CFMe₂ CH₂-c-PrN═CHNMe-Ph A2 2-NO₂ racemate 5-64 CFMe₂ CH₂-c-Pr N═CHNMePh A2 — racemate5-65 CFMe₂ CH₂-c-Pr N═C(Me)NMe₂) A2 — racemate 5-66 CFMe₂ CH₂-c-PrN═C(NMe₂)(NMeNMe₂) A2 — racemate 5-67 CFMe CH₂-c-Pr N═C(NEt₂)(NMeNMe₂)A2 — racemate 5-68 CH₂F CH₂-c-Pr N═C(SMe)(NMe₂) A2 — racemate 5-69 CH₂FCH₂-c-Pr N═C(SMe)(NMeOMe) A2 — racemate 5-70 CH₂F CH₂-c-PrN═C(SMe)(NMeNMe₂) A2 — racemate 5-71 CH₂CH₂CF₃ CH₂-c-Pr N═C(Et)(NHNH₂)A2 — racemate 5-72 CH₂CH₂CF₃ CH₂-c-Pr NH—N═CH—NMeOMe A2 — racemate 5-73CH₂CH₂CF₃ CH₂-c-Pr NH—N═CHNMeSMe A2 — racemate 5-74 H CH₂-c-Pr N═CH—NMe₂A2 — racemate

[0333] TABLE 6 Physical data and stereo- chemical No. R¹ A²-R² R³ A¹(X)_(n) information 6-1 CHFMe 3-furyl N═CHNMe₂ A2 — racemate 6-2 CHFMe3-furyl N═C(Me)(NMe₂) A2 — racemate 6-3 CHFMe 3-furyl N═C(Et)(NMe₂) A2 —racemate 6-4 CHFMe 3-furyl N═CHNEt₂ A2 — racemate 6-5 CFMe₂ 3-furylN═CMeNMe₂ A2 — racemate 6-6 CFMe₂ 3-furyl N═CHNMe₂ A2 — racemate

[0334] TABLE 7 Physical data and stereochemical No. R¹ A²-R² R³ A¹(X)_(n) information 7-1 CFMe₂

N═CHNMe₂ A2 — racemate 7-2 CFMe₂

N═CHNMe₂ A2 3-Me racemate 7-3 CFMe₂

N═CHNMe₂ A2 3,5-Me₂ racemate

[0335] TABLE 8 Physical data and stereochemical No. R¹ A²-R² R³ A¹(X)_(n) information 8-1  c-Pr c-Pr N═CHNMe₂ A3 — racemate 8-2  CFMe₂c-Pr N═CHNMe₂ A3 — racemate, oil 8-3  CF₃ c-Pr N═CHNMe₂ A3 3,5-Cl₂racemate 8-4  CF₂CF₃ c-Pr N═CHNMe₂ A3 — racemate 8-5  CFMe₂ c-PrN═CHNMe₂ A3 3-CF₃ racemate 8-6  CFMe₂ c-Pr N═CHNMe₂ A3 2-F racemate 8-7 CFMe₂ c-Pr N═CHNMe₂ A3 4-F racemate 8-8  CFMe₂ c-Pr N═CHNMe₂ A3 4-OCF₃racemate 8-9  CFMe₂ c-Pr N═CHNMe₂ A3 4-Cl racemate 8-10 CH₂F c-PrN═CHNEt₂ A3 — racemate 8-11 CFMe₂ c-Pr N═CHNEt₂ A3 — racemate, oil 8-12CFMe₂ c-Pr N═CHNEt₂ A3 4-F, 3-Me racemate 8-13 CFMe₂ c-Pr N═CHNEt₂ A33-Et racemate 8-14 CHFMe c-Pr N═CHNEt₂ A3 — racemate 8-15 CHFEt c-PrN═CHNEt₂ A3 — racemate 8-16 CHFPr c-Pr N═CHNEt₂ A3 — racemate 8-17 CFMe₂c-Pr N═CH—NMe₂ A3 3-Cl racemate 8-18 CHFMe c-Pr N═CH—NMe₂ A3 3-Clracemate 8-19 CHFEt c-Pr N═CH—NMe₂ A3 3-Cl racemate 8-20 CFMe₂ c-PrN═C(Me)(NMe₂) A3 3-F racemate, oil 8-21 CHFMe c-Pr N═C(Me)(NMe₂) A3 3-Fracemate, oil 8-22 CHFEt c-Pr N═C(Me)(NMe₂) A3 3-F racemate 8-23 CHMe₂c-Pr N═CH—NEt₂ A3 3-OMe racemate 8-24 CFMe₂ c-Pr N═CH—NEt₂ A3 3-OMeracemate 8-25 CHFMe c-Pr N═CH—NEt₂ A3 3-OMe racemate 8-26 CHFEt c-PrN═CH—NEt₂ A3 3-OMe racemate 8-27 CFMe₂ c-Pr NH—CH═N—OH A3 — racemate8-28 CFMe₂ c-Pr NH—CH═N—NH₂ A3 — racemate, oil 8-29 CFMe₂ c-PrNH—CH═N—NMe₂ A3 — racemate 8-30 CFMe₂ c-Pr N═CH(Me)(Ph) A3 — racemate8-31 CFMe₂ c-Pr N═CH(Ph)₂ A3 — racemate 8-32 CFMe₂ c-Pr N═CH(2-Cl—C₆H₄)₂A3 — racemate 8-33 CFMe₂ c-Pr N═CH(Me)(4-NO₂—C₆H₄) A3 — racemate 8-34CFMe₂ c-Pr N═CH(Et)(Ph) A3 — racemate 8-35 CFMe₂ c-Pr N═CH(n-Pr)(Ph) A3— racemate 8-36 CHFMe c-Pr N═CH(3-Cl—C₆H₄) A3 — racemate 8-37 CFMe₂ c-PrN═CH(4-Cl—C₆H₄) A3 — racemate, oil 8-38 CFMe₂ c-Pr N═CH—NMe₂ OA2 —racemate 8-39 CMe═CH₂ c-Pr N═CH—NMe₂ OA2 — racemate 8-40 CF₃ c-PrN═CH—NMe₂ OA2 — racemate 8-41 CHF₂ c-Pr N═CH—NMe₂ OA2 — racemate 8-42CHF₂ c-Pr N═CH—NMe₂ OA2 — racemate 8-43 CF₃ c-Pr N═CH—NMe₂ OA2 3,5-Me₂racemate 8-44 CCl₃ c-Pr N═CH—NMe₂ OA2 3-Et racemate 8-45 CFCe₂ c-PrN═CH—NMe₂ OA2 — racemate 8-46 Me c-Pr N═C(NMe₂)₂ OA2 — racemate 8-47 Mec-Pr N═C(NEt₂)₂ OA2 — racemate 8-48 i-Pr c-Pr N═C(NMe₂)(NEt₂) OA2 —racemate 8-49 i-Bu c-Pr N═C(NMe₂)(NMeOMe) OA2 — racemate 8-50 sec-Buc-Pr N═C(NEt₂)(NEtOEt) OA2 — racemate 8-51 n-Bu c-Pr N═C(NMe₂)(NMeSMe)OA2 — racemate 8-52 CF₂CHF₂ c-Pr N═C(OMe)(NMeOMe) OA2 — racemate 8-53CFMe₂ c-Pr N═CH—NMe₂ A3 — R enantiomer 8-54 CFMe₂ c-Pr N═CH—NMe₂ A3 — Senantiomer 8-55 CFMe₂ c-Pr N═CHNEt₂ A3 — R enantiomer 8-56 CFMe₂ c-PrN═CHNEt₂ A3 — S enantiomer 8-57 CFMe₂ c-Pr N═CHNMe₂ A3 3-F racemate, oil8-58 CHFMe c-Pr N═CHNMe₂ A3 3-F racemate, oil 8-59 CFMe₂ c-Pr N═CHNEt₂A3 3-F racemate, oil

[0336] TABLE 9 Physical data and stereo- chemical No. R¹ A²-R² R³ A¹(X)_(n) information 9-1 CFMe₂ c-Bu N═CH—NMe₂ A3 — racemate 9-2 CHMe₂c-Bu N═CH—NMe₂ A3 — racemate 9-3 CHFMe c-Bu N═CH—NMe₂ A3 — racemate 9-4CHFMe c-Bu N═CH—NMe₂ OA2 — racemate 9-5 CF₃ c-Bu N═C(Me)(NPr₂) OA2 —racemate

[0337] TABLE 10 Physical data and No. R¹ A²-R² R³ A¹ (X)_(n)stereochemical information 10-1 CH₂OEt c-Pr N═C(Ph)(NMe₂) A4 — racemate10-2 4-Cl—C₆H₄ c-Pr N═C(Bu)(NMe₂) A4 — racemate 10-3 c-Pr c-PrN═C(Me)(NEt₂) A4 — racemate 10-4 c-Bu c-Pr N═CHN(CH₂Ph)₂ A4 — racemate10-5 CFMe₂ c-Pr N═CHNMe₂ A4 — racemate 10-6 CFMe₂ c-Pr N═CHNMe₂ OA3 —racemate

[0338] TABLE 11 Physical data and No. R¹ A²-R² R³ A¹ (X)_(n)stereochemical information 11-1 Me Ph N═CH—NEt₂ A2 — racemate 11-2 Me PhN═CH—NEt₂ A2 3,5—Cl₂ racemate 11-3 Me 4-CF₃—C₆H₄ N═CH—NMe₂ OA1 —racemate 11-4 CFMeEt CH₂Ph N═CH—NMe₂ OA1 — racemate 11-5 CFMeEt4-CN—C₆H₄ N═CH—NMe₂ OA2 — racemate

[0339] TABLE 12 Compounds of the formula

Physical data and stereochemical No. R¹ A²-R² R³ Z (X)_(n) information12-1 CFMe₂ c-Pr N═CH—NMe₂ H — racemate 12-2 CHFMe c-Pr N═CH—NMe₂ H —racemate 12-3 CFMe₂ c-Pr N═CH—NMe₂ H 3-Cl racemate 12-4 CFMe₂ c-PrN═CH—NMe₂ H 3-F racemate 12-5 CFMe₂ c-Pr N═CH—NMe₂ H 3-CH₃ racemate 12-6CFMe₂ c-Pr N═CH—NMe₂ H 3-OCH₃ racemate 12-7 CHEMe c-Pr N═CH—NMe₂ H 3-Clracemate 12-8 CHFMe c-Pr N═CH—NMe₂ H 3-F racemate 12-9 CHFMe c-PrN═CH—NMe₂ H 3-CH₃ racemate 12-10 CHFMe c-Pr N═CH—NMe₂ H 3-OCH₃ racemate12-11 CFMe₂ c-Pr N═CH—NMe₂ F H racemate 12-12 CFMe₂ c-Pr N═CH—NMe₂ F3-Cl racemate 12-13 CFMe₂ c-Pr N═CH—NMe₂ F 3-F racemate 12-14 CFMe₂ c-PrN═CH—NMe₂ F 3-Me racemate 12-15 CFMe₂ c-Pr N═CH—NMe₂ F 3-OMe racemate12-16 CHFMe c-Pr N═CH—NMe₂ F — racemate 12-17 CHFMe c-Pr N═CH—NMe₂ F —racemate 12-18 CHFMe c-Pr N═CH—NMe₂ F — racemate 12-19 CHFMe c-PrN═CH—NMe₂ F — racemate 12-20 CFMe₂ c-Pr N═CHNEt₂ H — racemate 12-21CFMe₂ c-Pr N═C(Me)NEt₂ H — racemate 12-22 CFMe₂ c-Pr N═C(Me)NPr₂ H —racemate 12-23 CHFMe c-Pr N═CH—NEt₂ H — racemate 12-24 CHFEt c-PrN═CH—NEt₂ H — racemate 12-25 CHFEt c-Pr N═CH—NEt₂ Me — racemate 12-26CHFMe c-Pr N═CH—NEt₂ Me — racemate 12-27 CFMe c-Pr N═CH—NEt₂ Me —racemate 12-28 CHF₂ c-Pr N═CH—NEt₂ Et 3,5-(OEt)₂ racemate 12-29 CFMe₂c-Bu N═CH—NMe₂ H — racemate 12-30 CHFMe c-Bu N═CH—NMe₂ H — racemate12-31 CHFEt c-Bu N═CH—NMe₂ H — racemate 12-32 CHFPr c-Bu N═CH—NMe₂ H —racemate 12-33 CFMe₂ c-Bu N═CH—NMe₂ H — racemate 12-34 CFMe₂ c-BuN═CH—NMe₂ F — racemate 12-35 CFMe₂ c-Bu N═CH—NMe₂ Cl — racemate 12-36CFMe₂ c-Bu N═CH—NMe₂ Br — racemate 12-37 CFMe₂ c-Bu N═CH—NMe₂ Me —racemate 12-38 CFMe₂ c-Bu N═CH—NMe₂ Et — racemate 12-39 CHFMe c-BuN═CH—NMe₂ H — racemate 12-40 CHFMe c-Bu N═CH—NMe₂ F — racemate 12-41CHMe c-Bu N═CH—NMe₂ Me — racemate 12-42 CFMe₂ c-Bu N═CH—Net₂ H —racemate 12-43 CHFEt c-Bu N═CH—Net₂ F — racemate 12-44 CF₃ c-BuN═CH—Net₂ Me — racemate 12-45 CF₃ c-Bu N═C(Me)(NMe₂) H — racemate 12-46CF₂Me c-Bu N═C(Me)(NMe₂) H — racemate 12-47 CFMe₂ c-Bu N═C(Me)(NMe₂) H —racemate 12-48 CFMe₂ c-Bu N═C(Me)(NMe₂) 4-F, 3-Me racemate 12-49 CFMe₂c-Bu N═C(Et)(NEt₂) 4-F, 3-Me racemate

B. FORMULATION EXAMPLES

[0340] a) A dust is obtained by mixing 10 parts by weight of a compoundof the formula (I) and 90 parts by weight of talc as inert substance andcomminuting the mixture in a hammer mill.

[0341] b) A wettable powder which is readily dispersible in water isobtained by mixing 25 parts by weight of a compound of the formula (I),64 parts by weight of kaolin-containing quartz as inert material, 10parts by weight of potassium lignosulfonate and 1 part by weight ofsodium oleoylmethyltaurate as wetter and dispersant and grinding themixture in a pinned-disk mill.

[0342] c) A dispersion concentrate which is readily dispersible in wateris obtained by mixing 20 parts by weight of a compound of the formula(I) with 6 parts by weight of alkylphenol polyglycol ether ®Triton X207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71parts by weight of paraffinic mineral oil (boiling range for exampleapprox. 255 to over 277° C.) and grinding the mixture in a grinding-ballmill to a fineness of below 5 microns.

[0343] d) An emulsifiable concentrate is obtained from 15 parts byweight of a compound of the formula (I), 75 parts by weight ofcyclohexanone as solvent and 10 parts by weight of oxethylatednonylphenol as emulsifier.

[0344] e) Water-dispersible granules are obtained by mixing 75 parts byweight of a compound of the formula (I), 10 parts by weight of calciumlignosulfonate,  5 parts by weight of sodium laurylsulfate,  3 parts byweight of polyvinyl alcohol and  7 parts by weight of kaolin,

[0345] grinding the mixture on a pinned-disk mill and granulating thepowder in a fluidized bed by spraying on water of granulation liquid.

[0346] f) Water-dispersible granules are also obtained by homogenizingand precomminuting 25 parts by weight of a compound of the formula (I), 5 parts by weight 2,2′-dinaphthylmethane-6,6′-disulfonate,  2 parts byweight sodium oleoylmethyltaurate,  1 part by weight of polyvinylalcohol, 17 parts by weight of calcium carbonate and 50 parts by weightof water

[0347] in a colloid mill, subsequently grinding the mixture in a beadmill and atomizing and drying the resulting suspension in a spray towerby means of a single-substance nozzle.

C. BIOLOGICAL EXAMPLES

[0348] 1. Pre-Emergence Herbicidal Action

[0349] Seeds or rhizome pieces of monocotyledonous and dicotyledonousweed plants are placed in sandy loam in plastic pots and covered withsoil. The compounds according to the invention, which are formulated inthe form of wettable powders or emulsion concentrates, are then appliedto the surface of the soil cover as aqueous suspension or emulsion atvarious dosages with an application rate of 600 to 800 l of water per ha(converted).

[0350] After the treatment, the pots are placed into a greenhouse andkept under good growth conditions for the weeds. The plant or emergencedamage is scored visually after the test plants have emerged after anexperimental time of 3 to 4 weeks by comparison with untreated controls.

[0351] The compounds according to the invention show a very goodpre-emergence activity against a broad spectrum of grass weeds andbroad-leaved weeds. For example, compounds according to the invention(see Examples A1 to A3 and compounds 2-1, 2-35, 2-36, 245, 2-55, 2-56,3-1,3-14, 3-25, 3-37, 3-38, 340, 341, 343, 344, 346, 347,3-55, 3-56,3-58, 3-59, 3-67, 3-68, 3-70, 3-71, 3-74, 3-85, 3-86, 3-124, 5-1, 540,8-2,8-11, 8-20, 8-21, 8-27 and 8-37 of Tables 1 to 12) effect a verygood pre-emergence control on harmful plants such as Stellaria media,Lolium multiforum, Amaranthus retroflexus, Sinapis alba, Avena sativaand Setaria viridis.

[0352] 2.. Post-Emergence Herbicidal Action

[0353] Seeds or rhizome pieces of monocotyledonous and dicotyledonousweeds are placed in sandy loam in plastic pots, covered with soil andgrown in the greenhouse under good growth conditions. Three weeks aftersowing, the test plants are treated in the three-leaf stage. Variousdosages of the compounds according to the invention, which areformulated as wettable powders or emulsion concentrates, are sprayed tothe green plant parts at an application rate of 600 to 800 l of waterper ha (converted). After the test plants have been left to stand in thegreenhouse for approx. 3 to 4 weeks under optimal growth conditions, theeffect of the preparations is scored visually by comparison withuntreated controls. The compositions according to the invention alsohave a good herbicidal post-emergence activity against a broad spectrumof economically important grass weeds and broad-leaved weeds, forexample against harmful plants such as Sinapis alba, Echinochloacrus-galli, Lolium multiflorum, Stellaria media, Cyperus iria,Amaranthus retroflexus, Setaria viridis and Avena sativa when anapplication rate of 1 kg and less active substance of the compoundsaccording to the invention (see Examples A1 to A3 and compounds2-1,2-35, 2-36, 245, 2-55, 2-56, 3-1,3-14, 3-25, 3-37, 3-38, 340, 341,343, 344, 346, 3-47, 3-55, 3-56, 3-58, 3-59, 3-67, 3-68, 3-70, 3-71,3-74, 3-85, 3-86, 3-124, 5-1, 540, 8-2,8-11, 8-20, 8-21, 8-27 and 8-37of Tables 1 to 12) is applied post-emergence per hectare.

[0354] 3. Action Against Harmful Plants in Rice

[0355] Transplanted and seeded rice and typical rice weeds (broad-leavedand grass weeds) are grown in the greenhouse until they have reached thethree-leaf stage (Echinochloa crus-galli 1.5-leaves) under paddy riceconditions (flooding level of the water: 2-3 cm) in closed plastic pots.They are then treated with the compounds according to the invention. Tothis end, the formulated active substances are suspended, dissolved oremulsified in water and applied to the paddy water of the test plants atvarious dosages by application by pouring. After the treatment has beencarried out in this way, the test plants are placed into the greenhouseunder optimal growth conditions and kept in this way over the entireexperimental period.

[0356] Approximately three weeks after application, the experiments areevaluated by visually scoring the plant damage in comparison withuntreated controls. The compounds according to the invention (seeExamples A1 to A3 and compounds 2-1, 2-35, 2-36, 245, 2-55, 2-56,3-1,3-14, 3-25, 3-37, 3-38, 340, 341, 343, 344, 346, 347, 3-55, 3-56,3-58, 3-59, 3-67, 348, 3-70, 3-71, 3-74, 3-85,3-86, 3-124, 5-1, 540,8-2,8-11, 8-20, 8-21, 8-27 and 8-37 of Tables 1 to 12) show a very goodherbicidal action against harmful plants such as, for example, Cyperusmonti, Echinochloa crusgalli and Sagittaria pygmaea.

[0357] 4. Crop Plant Tolerance

[0358] In further greenhouse experiments seeds of a larger number ofcrop plants and weeds are placed in sandy loam covered with soil. Someof the pots are coated immediately as described in Section 1, while theremaining pots are placed in the greenhouse until the plants havedeveloped two to three leaves and are then sprayed with various dosagesof the substances of formula (I) according to the invention as describedunder Section 2. Four to five weeks after the application and standingtime in the greenhouse, it is found by means of visual scoring that thecompounds according to the invention leave dicotyledonous crops such as,for example, soybeans, cotton, oilseed rape, sugar beet and potatoesunharmed when applied pre- and post-emergence, even at high rates ofactive substance. In addition, some substances also leave graminaceouscrops such as, for example, barley, wheat, rye, sorghum, maize or rice,unharmed. Some of the compounds of the formula (I) show a high degree ofselectivity and are therefore suitable for controlling undesiredvegetation in agricultural crops.

1. A compound of the formula (I) or a salt thereof

in which R¹ is aryl, aryloxy, arylthio, arylamino,N-aryl-N-(C₁-C₄)alkylamino, (C₃-C₉)cycloalkyl, (C₃-C₉)cycloalkyloxy,(C₃-C₉)cycloalkylthio, (C₃-C₉)cycloalkylamino,N-(C₃-C₉)cycloalkyl-N-(C₁-C₄)alkylamino, di-[(C₃-C₉)cycloalkyl]amino,heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino orN-heterocyclyl-N-(C₁-C₄)alkylamino, where each of the last-mentioned 16radicals is unsubstituted or substituted, or is hydrogen, (C₁-C₆)alkyl,(C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₁-C₆)alkoxy, (C₂-C₆)alkenyloxy,(C₂-C₆)alkynyloxy, (C₁-C₆)alkylthio, (C₂-C₆)alkenylthio,(C₂-C₆)alkynylthio, (C₁-C₆)alkylamino or di-[(C₁-C₆)alkyl]amino, whereeach of the last-mentioned 11 radicals can be unsubstituted orsubstituted by one or more radicals selected from the group consistingof-halogen, hydroxyl, cyano, nitro, thiocyanato, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₂-C₄)alkenyloxy, (C₂-C₄)haloalkenyloxy,(C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylthio, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)haloalkylsulfonyl, (C₃-C₉)cycloalkyl which is unsubstituted orsubstituted, phenyl which is unsubstituted or substituted, heterocyclylwhich is unsubstituted or substituted, and radicals of the formulaeR′—C(═Z′)—, R′—C(═Z′)-Z-, R′-Z-C(═Z′)—, R′R″N—C(═Z′)—, R′-Z-C(═Z′)—O—,R′R″N—C(═Z′)-Z-, R′-Z-C(═Z′)—NR″— and R′R″N—C(═Z′)—NR′″—, where R′, R″and R′″ in each case independently of one another are hydrogen(C₁-C₆)alkyl, aryl, aryl-(C₁-C₆)alkyl, (C₃-C₉)cycloalkyl or(C₃-C₉)cycloalkyl-(C₁-C₆)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted, and where Z and Z′independently of one another are in each case an oxygen or sulfur atom,R² is (C₃-C₉)cycloalkyl which is unsubstituted or substituted,(C₄-G₉)cycloalkenyl which is unsubstituted or substituted, heterocyclylwhich is unsubstituted or substituted, or phenyl which is unsubstitutedor substituted, R³ is a group

in which L¹ is a direct bond, —O—, —S— or a group of the formula —NG²-,U¹, U² independently of one another are a group of the formula G³, OG⁴,SG⁵, NG⁶G⁷, NG⁸NG⁹G¹⁰, NG¹¹OG¹² or NG¹¹SG¹², U³ is a group of theformula G¹³, OG¹⁴, SG¹⁵, NG¹⁶G¹⁷, NG¹⁸NG¹⁹G²⁰, NG²¹OG² or NG²³SG²⁴, U⁴is a group of the formula G²⁵, OG²⁶, SG²⁷ or NG²⁸G²⁹, where the radicalsG¹ to G²⁹ independently of one another are hydrogen, aryl which isunsubstituted or substituted or (C₃-C₉)cycloalkyl which is unsubstitutedor substituted, or heterocyclyl which is substituted or unsubstituted,or are (C₁-C₆)alkyl, (C₂-C₆)alkenyl or (C₂-C₆)alkynyl, where each of thelast-mentioned 3 radicals is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, hydroxyl, cyano,nitro, thiocyanato, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₂-C₄)alkenyloxy,(C₂-C₄)haloalkenyloxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)haloalkylsulfonyl, (C₃-C₉)cycloalkyl which is unsubstituted orsubstituted, phenyl which is unsubstituted or substituted, heterocyclylwhich is unsubstituted or substituted, and radicals of the formulaeR′—C(═Z′)—, R′—C(═Z′)-Z-, R′-Z-C(═Z′)—, R′R″N—C(═Z′)—, R′-Z-C(═Z′)—O—,R′R″N—C(═Z′)Z—, R′-Z-C(═Z′)—NR″— and R′R″N—C(═Z′)—NR′″—, where R′, R″and R′″ in each case independently of one another are hydrogen,(C₁-C₆)alkyl, aryl, aryl-(C₁-C₆)alkyl, (C₃-C₉)cycloalkyl or(C₃-C₉)cycloalkyl-(C₁-C₆)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted and where Z and Z′independently of one another are in each case an oxygen or sulfur atom,and, inclusive of substituents, preferably has 1 to 30 carbon atoms, orthe radicals U¹ and U³ or U² and U⁴ or U² and G¹ or U⁴ and G¹, as apair, together with the atoms linking them are in each case acarbocyclic or heterocyclic ring having 4 to 7 ring atoms, the ringbeing unsubstituted or substituted, R⁴ is a radical of the formula—B¹-D⁴, where B¹ and D¹ are as defined hereinbelow, A¹ is a direct bondor straight-chain alkylene having 1 to 5 carbon atoms or straight-chainalkenylene or alkynylene having in each case 2 to 5 carbon atoms, whereeach of the three last-mentioned diradicals is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, nitro, cyano, thiocyanato and radicals of the formula—B²-D², where B² and D² are as defined hereinbelow, A² is a direct bondor straight-chain alkylene having 1 to 4 carbon atoms or straight-chainalkenylene or alkynylene having in each case 2 to 5 carbon atoms, whereeach of the three last-mentioned diradicals is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, nitro, cyano, thiocyanato and radicals of the formula—B³-D³, or a divalent radical of the formula V¹, V², V³, V⁴ or V⁵,CR^(a)R^(b)—W—CR^(c)R^(d)—  (V¹)CR^(a)R^(b)—W*—CR^(c)R^(d)—CR^(e)R^(f)—  (V²) —CR^(a)R^(ba—CR)^(c)R^(d)—W*—CR^(e)R^(f)—  (V³) —CR^(a)R^(b)—CR^(c)CR^(d)—W*—  (V⁴)—CR^(a)R^(b)—W*—  (V⁵) where each of the radicals R^(a), R^(b), R^(c),R^(d), R^(e) and R^(f) in each case independently of one another ishydrogen, halogen, nitro, cyano, thiocyanato or a radical of the formula—B⁴-D⁴, W* is in each case an oxygen atom, a sulfur atom or a group ofthe formula N(B⁵-D⁵) and B³, B⁴, B⁵, D³, D⁴ and D⁵ are as definedhereinbelow, B¹ and B⁵ in each case independently of one another are adirect bond or a divalent group of the formulae —C(═Z*)—, —C(═Z*)Z**-,—C(═Z*)—NH— or —C(═Z*)—NR*—, where Z*=an oxygen or sulfur atom, Z**=anoxygen or sulfur atom and R*=(C₁-C₆)alkyl, aryl, aryl-(C₁-C₆)alkyl,(C₃-C₉)cycloalkyl or (C₃-C₉)cycloalkyl-(C₁-C₆)alkyl, where each of the 5last-mentioned radicals is unsubstituted or substituted, B², B³ and B⁴in each case independently of one another are a direct bond or adivalent group of the formulae —O—, —S(O)_(p)—, —S(O)_(p)—O—,—O—S(O)_(p)—, —CO—, —O—CO—, —CO—O—, —S—CO—, —CO—S—, —S—CS—, —CS—S—,—O—CO—O—, —NR^(O)—, —O—NR^(O)—, —NR^(O)—O—, —NR^(O)—CO—, —CO—NR^(O)—,—O—CO—NR^(O)— or —NR^(O)—CO—O—, where p is the integer 0, 1 or 2 andR^(O) is hydrogen, (C₁-C₆)alkyl, aryl, aryl-(C₁-C₆)alkyl,(C₃-C₉)cycloalkyl or (C₃-C₉)cycloalkyl-(C₁-C₆)alkyl, where each of the 5last-mentioned radicals is unsubstituted or substituted, D¹, D², D³, D⁴and D⁵ in each case independently of one another are hydrogen,(C₁-C₆)alkyl, aryl, aryl-(C₁-C₆)alkyl, (C₃-C₉)cycloalkyl or(C₃-C₉)cycloalkyl-(C₁-C₆)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted, or in each case two radicalsD³ of two groups —B³-D³ bound to one carbon atom are linked to eachother and form an alkylene group having 2 to 4 carbon atoms which isunsubstituted or substituted by one or more radicals selected from thegroup consisting of (C₁-C₄)alkyl and (C₁-C₄)alkoxy, L^(o) is a directbond, oxygen, sulfur or a group NG³⁰ in which the radical G³⁰ ishydrogen, aryl which is unsubstituted or substituted, or(C₃-C₉)cycloalkyl which is unsubstituted or substituted, or heterocyclylwhich is substituted or unsubstituted, or (C₁-C₆)alkyl, (C₂-C₆)alkenylor (C₂-C₆)alkynyl, where each of the last-mentioned 3 radicals isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, hydroxyl, cyano, nitro, thiocyanato,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₂-C₄)alkenyloxy,(C₂-C₄)haloalkenyloxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)haloalkylsulfonyl, (C₃-C₉)cycloalkyl which is unsubstituted orsubstituted, phenyl which is unsubstituted or substituted, heterocyclylwhich is unsubstituted or substituted, and radicals of the formulaeR′—C(═Z′)—, R′—C(═Z′)-Z-, R′-Z-C(═Z′)—, R′R″N—C(═Z′)—, R′-Z-C(═Z′)—O—,R′R″N—C(═Z′)-Z-, R′-Z-C(═Z′)—NR″— and R′R″N—C(═Z′)—NR′″—, where R′, R″and R′″ in each case independently of one another are hydrogen,(C₁-C₆)alkyl, aryl, aryl-(C₁-C₆)alkyl, (C₃-C₉)cycloalkyl or(C₃-C₉)cycloalkyl-(C₁-C₆)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted and where Z and Z′independently of one another are in each case an oxygen or sulfur atom,(X)_(n) is n substituents X, where the X in each case independently ofone another are halogen, hydroxyl, amino, nitro, formyl, carboxyl,cyano, thiocyanato, aminocarbonyl or (C₁-C₆)alkyl, (C₁-C₆)alkoxy,(C₁-C₆)alkylthio, mono(C₁-C₆)alkylamino, di(C₁-C₄)alkylamino,(C₂-C₆)alkenyl, (C₂-C₆)alkynyl, [(C₁-C₆)alkyl]carbonyl,[(C₁-C₆)alkoxy]carbonyl, mono(C₁-C₆)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, N-(C₁-C₆)alkanoylamino orN-(C₁-C₄)alkanoyl-N-(C₁-C₄)alkylamino, where each of the last-mentioned13 radicals is unsubstituted or substituted,  or (C₃-C₉)cycloalkyl,(C₃-C₉)cycloalkoxy, (C₃-C₉)cycloalkylamino, phenyl, phenoxy, phenylthio,phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio orheterocyclylamino, where each of the last-mentioned 11 radicals isunsubstituted or substituted,  or two adjacent radicals X together are afused cycle having 4 to 6 ring atoms which is carbocyclic or containshetero ring atoms selected from the group consisting of O, S and N andwhich is unsubstituted or substituted by one or more radicals selectedfrom the group consisting of halogen, (C₁-C₄)alkyl and oxo, n is 0,1,2,3, 4 or 5 and heterocyclyl in the abovementioned radicalsindependently of one another in each case is a heterocyclic radicalhaving 3 to 7 ring atoms and 1 to 3 hetero atoms selected from the groupconsisting of N, O and S.
 2. A compound or a salt thereof as claimed inclaim 1, wherein R¹ is phenyl, phenoxy, phenylthio, phenylamino,N-phenyl-N-(C₁-C₄)alkylamino, where each of the last-mentioned 5radicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, hydroxyl, amino, nitro,formyl, carboxyl, sulfo, cyano, thiocyanato, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₉)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonyl and(C₁-C₄)haloalkylsulfonyl and, inclusive of substituents, has 6 to 30carbon atoms, or is (C₃-C₉)cycloalkyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, hydroxyl, amino, cyano, thiocyanato, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino and di(C₁-C₄)alkylamino and,inclusive of substituents, has 3 to 30 carbon atoms, or is heterocyclylwhich is unsubstituted or substituted by one or more radicals selectedfrom the group consisting of halogen, hydroxyl, amino, nitro, formyl,carboxyl, sulfonyl, cyano, thiocyanato, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₉)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxylcarbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonyl and(C₁-C₄)haloalkylsulfonyl and, inclusive of substituents, has 2 to 30carbon atoms, or is hydrogen or (C₁-C₆)alkyl, (C₂-C₆)alkenyl,(C₂-C₆)alkynyl, (C₁-C₆)alkoxy or (C₁-C₆)alkylthio, where each of thelast-mentioned 5 radicals is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, hydroxyl, cyano,nitro, thiocyanato, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₂-C₄)alkenyloxy,(C₂-C₄)haloalkenyloxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)haloalkylsulfonyland (C₃-C₆)cycloalkyl, which is unsubstituted or substituted by one ormore radicals selected from the group consisting of halogen, hydroxyl,amino, cyano, thiocyanato, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino and di(C₁-C₄)alkylamino, andphenyl and heterocyclyl, where each of the two last-mentioned radicalsis unsubstituted or substituted by one or more radicals selected fromthe group consisting of halogen, hydroxyl, amino, nitro, formyl,carboxyl, sulfonyl, cyano, thiocyanato, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₉)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, (C₁-C₄)alkylsulfonyl and(C₁-C₄)haloalkylsulfonyl, and radicals of the formulae R′—C(═Z′)—,R′—C(═Z′)-Z-, R′-Z-C(═Z′)—, R′R″N—C(═Z′)—, R′-Z-C(═Z′)—O—,R′R″N—C(═Z′)-Z-, R′-Z-C(═Z′)—NR″— and R′R″N—C(═Z′)—NR′″—, where R′, R″and R′″ in each case independently of one another are (C₁-C₄)alkyl,phenyl, phenyl(C₁-C₄)alkyl, (C₃-C₆)cycloalkyl or(C₃-C₆)cycloalkyl-(C₁-C₄)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, hydroxyl, amino, nitro,formyl, cyano, thiocyanato, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₂-C₄)alkenyl,(C₂-C₄)alkynyl, (C₃-C₆)cycloalkyl and, in the case of cyclic radicals,also (C₁-C₄)alkyl and (C₁-C₄)haloalkyl, and where Z and Z′ independentlyof one another are in each case one oxygen or sulfur atom, and R² is(C₃-C₉)cycloalkyl which is unsubstituted or substituted by one or moreradicals selected from the group consisting of the radicals A), B), C)and D), where group A) consists of the radicals halogen, hydroxyl,amino, nitro, formyl, carboxyl, aminocarbonyl, sulfo, cyano, thiocyanatoand oxo, group B) consists of the radicals (C₁-C₆)alkyl, (C₁-C₆)alkoxy,(C₁-C₆)alkylthio, mono(C₁-C₆)alkylamino, di(C₁-C₄)alkylamino,(C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₉)cycloalkyl, (C₄-C₉)cycloalkenyl,(C₁-C₆)alkylidene, (C₄-C₉)cycloalkylidene, radicals of the formulaeR′—C(═Z′)—, R′—C(═Z′)-Z-, R′-Z-C(═Z′)—, R′R″N—C(═Z′)—, R′-Z-C(═Z′)—O—,R′R″N—C(═Z′)-Z-, R′-Z-C(═Z′)—NR″— and R′R″N—C(═Z′)—NR′″—, where R′, R″and R′″ in each case independently of one another are hydrogen,(C₁-C₆)alkyl, phenyl, phenyl-(C₁-C₆)alkyl, (C₃-C₉)cycloalkyl or(C₃-C₉)cycloalkyl-(C₁-C₆)alkyl and where Z and Z′ independently of oneanother are in each case an oxygen or sulfur atom, group C) consists ofradicals as defined for group B), but where each radical is substitutedby one or more radicals selected from the group consisting of halogen,hydroxyl, amino, nitro, formyl, carboxyl, sulfo, cyano, thiocyanato,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₉)cycloalkyl, (C₄-C₉)cycloalkylene (C₄-C₉)cycloalkylidene,[(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl, aminocarbonyl,mono(C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl, phenyl,phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy,heterocyclylthio and heterocyclylamino, where each of the last-mentioned21 radicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, nitro, cyano,(C₁-C₄)alkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkoxy, formyl,(C₁-C₄)alkylcarbonyl and (C₁-C₄)alkoxycarbonyl and, in the case ofcyclic radicals, also (C₁-C₄)alkyl, (C₁-C₄)haloalkyl and(C₁-C₆)alkylidene,  and, in the case of cyclic radicals, also(C₁-C₆)alkyl, (C₁-C₆)haloalkyl and (C₁-C₆)alkylidene, and group D)consists of divalent or trivalent aliphatic bridges having 1 to 6,preferably 1 to 4, carbon atoms which, in the case of divalent bridges,connect two and, in the case of trivalent bridges, three carbon atoms ofthe cyclic skeleton and the radical R² thus constitutes the radical of abicyclic or tricyclic system, where each of the bridges is unsubstitutedor substituted by one or more substituents selected from the groupconsisting of halogen, nitro, cyano, (C₁-C₄)alkyl, (C₁-C₄)alkoxy,(C₁-C₄)alkylthio, (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, formyl,(C₁-C₄)alkylcarbonyl, (C₁-C₄)alkoxycarbonyl and oxo,  and where R²,inclusive of substituents, has 3 to 20 carbon atoms, or R² is(C₄-C₉)cycloalkenyl which is unsubstituted or substituted by one or moreradicals selected from the group consisting of the radicals A), B), C)and D) as are defined as radicals for the case whereR²=(C₃-C₉)cycloalkyl and, in this context, inclusive of substituents has4 to 20 carbon atoms, or R² is heterocyclyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof the radicals A), B), C) and D) as are defined as radicals for thecase where R²(C₃-C₉)cycloalkyl, or R² is phenyl which is unsubstitutedor substituted by one or more radicals selected from the groupconsisting of the radicals A), B) and C) as are defined as radicals forR²=(C₃-C₉)cycloalkyl, where R² inclusive of substituents has up to 20carbon atoms.
 3. A compound or a salt thereof as claimed in claim 1,wherein R³ is a radical of the formula

where R⁶ and R⁷ together with the nitrogen atom of the group NR⁶R⁷, R⁷and OR⁸ together with the nitrogen atom of the group NOR⁸R⁷, R⁷ and SR⁸together with the nitrogen atom of the group NSR⁸R⁷, R¹⁰ and R¹¹together with the nitrogen atom of the group NR¹⁰OR¹¹, OR¹² and OR¹³, orSR¹² and SR¹³, together with the carbon atom of the groups of theformulae

respectively, OR⁹ and R¹⁴ or SR⁹ and R¹⁴ together with the carbon atomof the groups

respectively, R¹⁴ and R¹⁵ together with the carbon atom of the group

R⁵ and R⁷ together with the atom group

R⁵ and R¹⁷ together with the carbon atom of the group

R⁵ and R¹⁶ together with the atom group

R⁷ and R¹⁰ together with the atom group

in each case independently of one another form a carbocyclic orheterocyclic ring having 3 to 7 ring atoms and 1 to 6 hetero atoms, theoptional further hetero ring atoms being selected from the groupconsisting of N, O and S and the carbocyclic or heterocyclic ring ineach case being unsubstituted or substituted, and the radicals R⁵, R⁶,R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹⁴ R¹⁵ R¹⁶, R¹⁷ in the above formulaeindependently of one another are hydrogen, aryl which is unsubstitutedor substituted, or (C₃-C₉)Cycloalkyl which is unsubstituted orsubstituted, or heterocyclyl which is unsubstituted or substituted, or(C₁-C₆)alkyl, (C₂-C₆)alkenyl or (C₂-C₆)alkynyl, where each of thelast-mentioned 3 radicals is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, hydroxyl, cyano,nitro, thiocyanato, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₂-C₄)alkenyloxy,(C₂-C₄)haloalkenyloxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)haloalkylsulfonyl, (C₃-C₉)cycloalkyl which is unsubstituted orsubstituted, phenyl which is unsubstituted or substituted, heterocyclylwhich is unsubstituted or substituted, and radicals of the formulaeR′—C(═Z′)—, R′—C(═Z′)-Z-, R′-Z-C(═Z′)—, R′R″N—C(═Z′)—, R′-Z-C(═Z′)—O—,R′R″N—C(═Z′)-Z-, R′-Z-C(═Z′)—NR″— and R′R″N—C(═Z′)—NR′″—, where R′, R″and R′″ in each case independently of one another are hydrogen,(C₁-C₆)alkyl, aryl, aryl-(C₁-C₆)alkyl, (C₃-C₉)cycloalkyl or(C₃-C₉)cycloalkyl-(C₁-C₆)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted and where Z and Z′independently of one another are in each case an oxygen or sulfur atom,and R¹² R¹³ in each case independently of one another are aryl which isunsubstituted or substituted, or (C₃-C₉)cycloalkyl which isunsubstituted or substituted, or heterocyclyl which is substituted orunsubstituted, or (C₁-C₆)alkyl, (C₂-C₆)alkenyl or (C₂-C₆)alkynyl, whereeach of the last-mentioned 3 radicals is unsubstituted or substituted byone or more radicals selected from the group consisting of halogen,hydroxyl, cyano, nitro, thiocyanato, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,(C₂-C₄)alkenyloxy, (C₂-C₄)haloalkenyloxy, (C₁-C₄)alkylthio,(C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)haloalkylsulfonyl, (C₃-C₉)cycloalkyl which is unsubstituted orsubstituted, phenyl which is unsubstituted or substituted, heterocyclylwhich is unsubstituted or substituted, and radicals of the formulaeR′—C(═Z′)—, R′—C(═Z′)-Z-, R′-Z-C(═Z′)—, R′R″N—C(═Z′)—, R′-Z-C(═Z′)—O—,R′R″N—C(═Z′)-Z-, R′-Z-C(═Z′)—NR″— and R′R″N—C(═Z′)—NR′″—, where R′, R″and R′″ in each case independently of one another are (C₁-C₆)alkyl,aryl, aryl(C₁-C₆)alkyl, (C₃-C₉)cycloalkyl or(C₃-C₉)cycloalkyl-(C₁-C₆)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted and where Z and Z′independently of one another are in each case one oxygen or sulfur atom,4. A compound or a salt thereof as claimed in claim 1, wherein R⁴ ishydrogen, (C₁-C₄)alkyl, phenyl or (C₃-C₆)cycloalkyl, where each of the 3last-mentioned radicals is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, hydroxyl, amino,nitro, formyl, carboxyl, sulfonyl, cyano, thiocyanato, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₃-C₉)cycloalkyl,[(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl, aminocarbonyl,mono(C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfonyl and, in the case ofcyclic radicals, also (C₁-C₄)alkyl and (C₁-C₄)haloalkyl, or is formyl,[(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl, aminocarbonyl,mono(C₁-C₄)alkylaminocarbonyl or di(C₁-C₄)alkylaminocarbonyl; and L^(o)is a direct bond or oxygen, A¹ is straight-chain alkylene having 1 to 5carbon atoms or straight-chain alkenylene or alkynylene having in eachcase 2 to 5 carbon atoms, where each of the three last-mentioneddiradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, nitro, cyano, thiocyanatoand a radical of the formula —B²-D², in which B² is a direct bond or adivalent group of the formulae —O—, —SO₂—, —CO—, —O—CO—, —NR^(O)—,—NR^(O)—CO—, —CO—NR^(O)—, —O—CO—NR^(O) or —NR^(O)—CO—O—, in which R^(O)independently of one another are in each case hydrogen, (C₁-C₄)alkyl,phenyl, phenyl-(C₁-C₄)alkyl, (C₃-C₆)cycloalkyl or(C₃-C₆)cycloalkyl-(C₁-C₄)alkyl, where each of the last-mentioned 5radicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, hydroxyl, amino, nitro,formyl, carboxyl, sulfonyl, cyano, thiocyanato, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₃-C₉)cycloalkyl,[(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl, aminocarbonyl,mono(C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfonyl and, in the case ofcyclic radicals, also (C₁-C₄)alkyl and (C₁-C₄)haloalkyl, A² is a directbond or a group of the formula —CH₂—, —CH₂CH₂—, —CH₂CH₂CH₂— or—CH₂CH₂CH₂CH₂—, where each of the 4 last-mentioned diradicals isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, nitro, cyano, thiocyanato and radicals ofthe formula —B³-D³, or a divalent radical of the formula V¹, V², V³, V⁴or V⁵, —CR^(a)R^(b)—W*—CR^(c)R^(d)—  (V¹)CR^(a)R^(b)—W*—CR^(c)R^(d)—CR^(e)R^(f)—  (V²)—CR^(a)R^(b)—CR^(c)R^(d)—W*—CR^(e)R^(f)—  (V³)—CR^(a)R^(b)—CR^(c)R^(d)—W*—  (V⁴) —CR^(a)R^(b)—W*—  (V⁵) where each ofthe radicals R^(a) to R^(f) in each case independently of one other ishydrogen, halogen, nitro, cyano, thiocyanato or a radical of the formula—B⁴-D⁴, W* is in each case O, S or a group of the formula N(B⁵-D⁵), andB⁵ is a direct bond or a divalent group of the formulae —C(═Z*)—,—C(═Z*)-Z**-, —C(═Z*)—NH— or —C(═Z*)—NR*—, where Z*=O or S, Z**=O or Sand R*=(C₁-C₄)alkyl, phenyl, phenyl-(C₁-C₄)alkyl, (C₃-C₆)cycloalkyl or(C₃-C₆)cycloalkyl-(C₁-C₄)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted, B², B³ and B⁴ in each caseindependently of one another are a direct bond or a divalent group ofthe formulae —O—, —S(O)_(p)—, —S(O)_(p)—O—, —O—S(O)_(p)—, —CO—, —O—CO—,—CO—O—, —S—CO—, —CO—S—, —S—CS—, —CS—S—, —O—CO—O—, —NR^(O)—, —O—NR^(O)—,—NR^(O)—O—, —NR^(O)—CO—, —CO—NR^(O)—, —O—CO—NR^(O)— or —NR^(O)—CO—O—,where p is the integer 0, 1 or 2 and R^(O)=hydrogen, (C₁-C₄)alkyl,phenyl, phenyl-(C₁-C₄)alkyl, (C₃-C₆cycloalkyl or(C₃-C₆)cycloalkyl-(C₁-C₄)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, hydroxyl, amino, nitro,formyl, carboxyl, sulfo, cyano, thiocyanato, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₃-C₉)cycloalkyl,[(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl, aminocarbonyl,mono(C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfonyl and, in the case ofcyclic radicals, also (C₁-C₄)alkyl and (C₁-C₄)haloalkyl, and D², D³, D⁴and D⁵ independently of one another are hydrogen, (C₁-C₆)alkyl, phenyl,phenyl-(C₁-C₄)alkyl, (C₃-C₆)cycloalkyl or(C₃-C₆)cycloalkyl-(C₁-C₆)alkyl, where each of the 5 last-mentionedradicals is unsubstituted or substituted.
 5. A compound or a saltthereof as claimed in claim 1, wherein (X)_(n) is n substituents X,where X preferably in each case independently of one another arehalogen, hydroxyl, amino, nitro, formyl, carboxyl, cyano, thiocyanato,aminocarbonyl or (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₂-C₄)alkenyl,(C₂-C₄)alkynyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,mono(C₁-C₄)alkylaminocarbonyl, di(C₁-C₄)alkylaminocarbonyl,N-(C₁-C₆)alkanoylamino or N-(C₁-C₄)alkanoyl-N-(C₁-C₄)alkylamino, whereeach of the last-mentioned 13 radicals is unsubstituted or substituted,preferably unsubstituted or substituted by one or more radicals selectedfrom the group consisting of halogen, hydroxyl, amino, cyano,thiocyanato, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkylamino, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl,di(C₁-C₄)alkylaminocarbonyl, phenyl, phenoxy, phenylthio,phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio andheterocyclylamino, where each of the last-mentioned 8 radicals isunsubstituted or has one or more substituents selected from the groupconsisting of halogen, nitro, cyano, (C₁-C₄)alkyl, (C₁-C₄)alkoxy,(C₁-C₄)alkylthio, (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy, formyl,(C₁-C₄)alkylcarbonyl and (C₁-C₄)alkoxycarbonyl,  or is(C₃-C₉)cycloalkyl, phenyl, phenoxy, phenylthio, phenylcarbonyl,heterocyclyl, heterocyclyloxy, heterocyclylthio or heterocyclylamino,where each of the last-mentioned 9 radicals is unsubstituted orsubstituted, preferably unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, hydroxyl, amino,nitro, formyl, carboxyl, cyano, thiocyanato, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)haloalkylthio, mono(C₁-C₄)alkylamino, di(C₁-C₄)alkylamino,(C₃-C₆)cycloalkyl, [(C₁-C₄)alkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,aminocarbonyl, mono(C₁-C₄)alkylaminocarbonyl anddi(C₁-C₄)alkylaminocarbonyl,  or two adjacent radicals X together are afused cycle having 4 to 6 ring atoms which is carbocyclic or containshetero ring atoms selected from the group consisting of O, S and N andwhich is unsubstituted or substituted by one or more radicals selectedfrom the group consisting of halogen, (C₁-C₄)alkyl and oxo, and n is 0,1, 2 or
 3. 6. A process for the preparation of a compound of the formula(I) or a salt thereof as defined in claim 1,

where A¹, A², L⁰, R¹, R², R³, R⁴, X and n are as defined in formula (I)in claim 1, wherein a) in the event that R³ in formula (I) is a group ofthe formula -L′-N═C(U¹)(U³), where L¹, U¹ and U³ are as defined under R³in formula (I), a compound of the formula (II)

 where A¹, A², L⁰, L¹, R¹, R², R⁴, X and n are as defined in formula(I), is reacted with a compound of the formula (III)

 where U¹ and U³ are as defined in formula (I) and R¹⁸ and R¹⁹independently of one another are unsubstituted or substituted alkylhaving up to 12 carbon atoms, or jointly linked are an alkylene grouphaving 2 to 4 carbon atoms, or b) in the event that R³ in formula (I) isa group of the formula L¹-NG¹-C(U²)═N—U⁴ where L¹, G¹, U² and U⁴ are asdefined under R³in formula (I), a compound of the formula (IV)

 where A¹, A², L⁰, L¹, R¹, R², R⁴, G¹, X and n are as defined in formula(I) in claim 1 is reacted with a compound of the formula (V)

 where U² and U⁴ are as defined in formula (I) and R¹⁸ is as defined informula (III) in variant a) of the present claim, or c) in the eventthat R³ in formula (I) is a group of the formula -L¹-N═C(U¹)(U³) whereU³=NG¹⁸NG¹⁹G²⁰, NG²¹OG²² or NG²³SG²⁴ and L¹, U¹, G¹⁸, G¹⁹, G²⁰, G²¹,G²², G²³, G²⁴ are as defined under R³ in formula (I), a compound of theformula (VI)

 where A¹, A², L⁰, L¹, R¹, R², R⁴, U¹, X and n are as defined in formula(I) and R⁶ and R⁷ are as defined under R³ in formula (I) are reactedwith a compound of the formula (VII) or its acid adducts H—U³  (VII) where U³ is as defined in formula (I), or d) in the event that R³ informula (I) is a group of the formula -L¹-N═C(U¹)(U³) where U¹=R¹⁴ andU³=R¹⁵ and where L¹, R¹⁴ and R¹⁵ are as defined under R³ in claim 3, acompound of the formula (II) as defined in variant a) of the presentclaim is reacted with an aldehyde or ketone of the formula (VIII)U¹—CO—U³  (VIII)  where U¹ and U³ are as defined in formula (I).
 7. Aherbicidal or plant-growth-regulating composition, which comprises oneor more compounds of the formula (I) or their salts as claimed in claims1 and formulation auxiliaries applicable in crop protection.
 8. A methodof controlling harmful plants or for regulating the growth of plants,which comprises applying an active amount of one or more compounds ofthe formula (I) or their salts as claimed in claim 1 to the plants,plant seeds or the area under cultivation.
 9. The use of compounds ofthe formula (I) or their salts as claimed in claim 1 as herbicides orplant growth regulators.
 10. The use as claimed in claim 9, wherein thecompounds of the formula (I) or their salts are employed for controllingharmful plants or for regulating the growth of crops of useful plants orornamentals.